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Having Thick Skin Is A 'Survival Technique,' Says Comic Jeff Ross

TERRY GROSS, HOST:

This is FRESH AIR. I'm Terry Gross. Today we conclude our series featuring some of our favorite interviews of 2016 with comic Jeff Ross, who is sometimes called The RoastMaster General. He's one of the producers of the Comedy Central celebrity roasts and has been a roaster on each one since 2005, hurling insulting punch lines at roastees such as William Shatner, Joan Rivers, Donald Trump, Charlie Sheen, James Franco, Justin Bieber and Rob Lowe. A new round of Ross' Comedy Central series "Roast Battle" started last night. He's done roasts in some pretty unusual places. In 2015, he did a comedy special roasting inmates in the Brazos County jail in Texas.

I spoke with Ross in September when Comedy Central was showing his special "Jeff Ross Roasts Cops" in which he roasted police in a Boston precinct. You can still watch that one on the Comedy Central website. We started with a clip from early on in his time at the police precinct before he'd won the trust of the cops. Ross is at the mic in front of the room while the police officers are standing all the way in back with their hands in their pockets, responding to each punch line with silence.

(SOUNDBITE OF TV SHOW, "JEFF ROSS ROASTS COPS")

JEFF ROSS: How are you, everybody? I'll make this quick because I know most of you are double parked. Thank you for letting me come here. This is really cool. I've never performed in front of an entire room full of YouTube celebrities before. This would be so much better if you guys just came into the middle of the [expletive] room. All right, fine. You guys also have a rich criminal history in this town. You had the Boston Tea Party here. Whitey Bulger was from here. Tom Brady is from here.

(BOOING)

ROSS: Oh, come on, that one really let the air out of the room, huh? Now, let's be real, if Whitey Bulger's name would have been Blackey Bulger, they would have caught him a lot quicker. (Laughter) Jesus Christ. There's obviously a problem between the cops and the community across the country right now, and that's what I'm here because that really bothers me. And it really bothers me when some people say that all cops are racist. Of course that's not true. Most of you are just [expletive] to everybody. (Laughter) All right, well, thanks for coming. All right.

(SOUNDBITE OF ARCHIVED BROADCAST)

GROSS: (Laughter) Jeff Ross, welcome to FRESH AIR. Those jokes were hilarious. It must have been so weird to have this room full of cops just glaring at you as you told these jokes. What was going wrong?

ROSS: (Laughter) You know, I didn't know for sure at the time why I was bombing so bad. I mean, that was one of the worst appearances of my career. It wasn't later till I found out that they were essentially protesting me for appearing at a rally in New York. Not great detectives.

GROSS: Well, you were appearing...

ROSS: They claimed I was a cop hater, so they wouldn't laugh at my jokes.

GROSS: The appearance that you show at that rally in your special is you talking to people about why they're there. You don't seem to be advocating for anything.

ROSS: I was doing my due diligence. I like to roast things from the inside out. I like to know what's going on. And I wanted to be fair. I wanted to be balanced. I wanted to show both sides of this issue, otherwise it would have been a fluff piece about cops and that would be boring.

GROSS: So how did you turn things around? Because by the end, everybody's laughing, everybody wants to be roasted by you.

ROSS: I bought them pizza. That helped. As they say in the show, a way to a cop's heart is through his stomach, and I stuck with it. And I think they appreciated my commitment, my tenacity in sticking with the plan. After I bombed in that first roll call, I immediately put on a vest and got in the back of a car with two cops named Jose (ph) and Izzy (ph) and I tried to learn what their job is really like. And I stayed out all night with them and did that for a week. And I think I essentially eventually earned their - some trust.

GROSS: Why did you want to roast cops?

ROSS: Well, everyone's been talking about the cops all over America. Very few people are engaging with the cops, and I didn't know why. And I wanted to find out what their job was really like, and what they would laugh at. I was curious. I've always liked cops, as much as you can like a group of people, you know? Sure, I've been hassled, but I'm a white dude - privileged. Like most white dudes, I didn't know really what was happening between the African-American community and the police community.

So I jumped into that rally, and I jumped into the Boston police force. I became a cop essentially for those - for that week, staying out with them and keeping their hours. And, you know, when we did talk to people on the street, a lot of them didn't recognize me right away and they talked to me as a cop. So that was fascinating. People are not afraid to be very direct with police. And I think that's part of the problem is that people are angry at the cops and then the cops are stressed out and they, you know, pay it backwards, so to speak.

GROSS: What did somebody say to you that helped you understand?

ROSS: I don't like you all. I don't trust you guys. (Laughter) You know, there's a lot of animosity there. But in Boston where community policing is so important, they don't necessarily have to like each other, but they know each other. The cops in Boston make it their business to get out of their vehicles, to engage the public, to walk around the neighborhoods. They live in the community that they police. And I think these things help.

GROSS: So in addition to recently roasting cops, you recently roasted prisoners at the Brazos County jail in Texas. And I want to play an example of that. You did comedy roast for the female prisoners and a separate one for the male prisoners. So here's Jeff Ross from his "Jeff Ross Roasts Criminals: Live At Brazos County Jail" performing to an audience of women in orange jumpsuits.

(SOUNDBITE OF TV SHOW, "JEFF ROSS ROASTS CRIMINALS: LIVE AT BRAZOS COUNTY JAIL")

ROSS: This must be hell, all these women wearing the same outfit.

(LAUGHTER)

ROSS: Orange is the new very black. Look at you.

(LAUGHTER)

ROSS: Man, you're beautiful. What's going on? Have you been in here long enough to find me attractive?

(LAUGHTER)

ROSS: Oh, and look at this. This is awesome. We got Justin Bieber here.

(LAUGHTER, APPLAUSE)

ROSS: Take a bow, take a bow. This is a trip for sure, man. I have never done a show for all women before, and I've never done a show inside a jail before. So this is huge for me.

(APPLAUSE)

ROSS: Thank you. The good thing about a jail show is nobody gets up and walks out.

(LAUGHTER)

GROSS: That's Jeff Ross at the Brazos County jail doing stand-up to an audience of women in the jail. So you kind of roasted yourself there, asking the inmates if they were there long enough to find you attractive.

(LAUGHTER)

GROSS: Is that allowable, to roast yourself and be self-deprecating in what's supposed to be a roast?

ROSS: I think, you know, before you can be all deprecating, Terry, it's helpful to be self-deprecating.

(LAUGHTER)

ROSS: And it's interesting. I hadn't heard that in a while, that clip, and it reminds me of some of the things that the jailers told me afterwards. And, you know, the women had not been spoken to as women in a long time is what the jailers told me. And, you know, they're spoken to as prisoners. We don't humanize them. They don't get to laugh like that, especially in a group. And I think it was cathartic for them, and that's what the jailers told me afterwards, that morale was really high and all the inmates, the men and women that I performed for down at Brazos County jail, they had to behave for a month in order to get into the show.

So it was fun for them. And they don't have a lot of fun. And a lot of people might be thinking right now, well, they shouldn't have fun. They're inmates, but they're people, and we forget that. Inside those orange jumpsuits is a beating heart, and they want to get home to somebody somewhere. And maybe I'm corny, but I'm a big believer in second chances. And there's a lot of very bad people at Brazos County jail, but there's also a lot of people who are going to get out. Ninety percent of all prisoners in all jails get out some day. So why not give them a little levity in what's otherwise a very dark life?

GROSS: If you're just joining us, my guest is Jeff Ross, and he has a new Comedy Central special called "Jeff Ross Roasts Cops." And Jeff Ross is one of the producers of the Comedy Central celebrity roast. Are there any rules for celebrity roasts about what's fair and what's out of bounds?

ROSS: You know, my own personal rule, Terry, is to tell jokes that I think the person I'm making them about can laugh at, to go home and tell their family, oh, my gosh. Guess what Jeff Ross said about me. And then they go and own that joke forever. I love that. I want the roast to be like a party where everybody goes and has a good time.

GROSS: Do you ever feel like people go too far or do you think that you've ever gone too far in a joke that you've made about someone?

ROSS: That's a good question. You know, I'm pretty careful about the things I say ahead of time. I'm thoughtful about not going too far. The only thing you can do occasionally is be too much. Like, I like to stick and move, Terry, there are one joke about everybody, one or two jokes about everybody. Every now and then I'll stop and do five or six if I have a really good target. Like we added Ann Coulter to this recent Rob Lowe roast, and she was sort of a last-minute addition. She wanted to promote her book. But I thought, well, you know, Rob Lowe is kind of a fun target, you know? But Ann Coulter, there's somebody I can really turn the heat up on. And she's a pundit. She's in politics. She can take it of course.

GROSS: Let's hear an example of what happened at the roast. So this was the Rob Lowe roast that happened in August. Ann Coulter was one of the people on the dais. And so she got to roast other people, and she got to be roasted. And so I want to play three people in a row talking about her. So...

ROSS: I love it.

GROSS: OK, so we're going to hear from in order Jimmy Carr, who's a British comic, Pete Davidson from "Saturday Night Live" and then the singer-songwriter Jewel.

(SOUNDBITE OF TV SHOW, "ROAST OF ROB LOWE")

JIMMY CARR: Ann Coulter. Here we go.

(LAUGHTER, CHEERING)

CARR: Ann Coulter is one of the most repugnant, hateful, hatchet-faced bitches alive.

(LAUGHTER)

CARR: But it's not too late to change, Ann. You could kill yourself.

(LAUGHTER)

CARR: Ann Coulter looks so much like a truck stop transvestite whore that I saw Jeff Ross run to an ATM just before the show.

(LAUGHTER)

PETE DAVIDSON: And Ann Coulter is here, everybody. Ann Coulter, if you're here, who's scaring the crows away from our crops?

(LAUGHTER)

DAVIDSON: You know, Ann describes herself as a polemicist, but most people call her a [expletive].

(LAUGHTER)

DAVIDSON: You know, last year, we had Martha Stewart who sells sheets and now we have Ann Coulter who cuts eye holes in them.

(LAUGHTER)

JEWEL: Thank you so much. It is an honor to be here. I do want to say, first of all, as a feminist, I can't support everything that's being said up here tonight. But as somebody that hates Ann Coulter, I'm delighted, so...

(LAUGHTER, CHEERING)

GROSS: OK. So that's people who are roasting Ann Coulter at the Rob Lowe roast. Then Ann Coulter gets up and speaks. And I'll play a short segment of what she had to say at the Rob Lowe roast. Here we go.

ROSS: (Laughter) Please don't.

(SOUNDBITE OF TV SHOW, "ROAST OF ROB LOWE")

ANN COULTER: I once thought Pete Davidson was just like Obama, biracial goofball who ruined a once-beloved institution, but it turns out I was wrong. Pete's not biracial.

(LAUGHTER)

DAVIDSON: Ha ha, good one.

COULTER: And now for the man of the hour.

(LAUGHTER, APPLAUSE)

GROSS: And that Pete Davidson yelling out, good one (laughter). The room got very cold when she spoke, yeah.

ROSS: The audience - see, she went on towards the end, and when we put someone up towards the end, it gives them a lot of goodwill because now she's been made fun of for an hour and a half. So she can go up and everybody is kind of rooting for her to come back. No one's thinking about her entire body of work in that moment. They're only looking to have a good time. It's a Saturday night in Hollywood, and instead of, like, kind of doing the material, the very self-aware material that our writers wrote for her, she decided to do her own thing, which was more divisive.

And the first thing she did was take her new book out and prop it up on the podium, so the whole thing came off as a book plug. She chastised the writers for, quote, "making me be mean" and she yelled at the teleprompter people. And so she showed no vulnerability at all and didn't seem to be having fun. And I think that's why her set maybe backfired. You know, she got some boos and so on. And listen (laughter) and now she's claiming that we edited it to make her look worse. So I'm not really sure what's happening in her brain. She was very lovely before the show. I did not get to see her afterwards, but I'm not worried about her, Terry. She's a very tough woman. I think she's the only woman ever to sexually harass Roger Ailes from Fox News.

GROSS: (Laughter) Well, she certainly knows how to dish it out. She's a professional provocateur, and she never holds back.

ROSS: Right, right.

GROSS: So my guess is Jeff Ross, who's known as The RoastMaster General. He's one of the producers of the Comedy Central celebrity roasts. And let's take a short break here. Then we'll talk some more. This is FRESH AIR.

(SOUNDBITE OF MUSIC)

GROSS: This is FRESH AIR. Let's get back to our interview with comic Jeff Ross, who's been a roaster on every Comedy Central celebrity roast since 2005. The latest was a roast of Rob Lowe. The roastmaster was David Spade. The roasters on the dais included Jeff Ross, Peyton Manning, Pete Davidson, Jewel, Jimmy Carr and Ann Coulter. So the Rob Lowe roast actually turned into a roast of Ann Coulter.

ROSS: It seems that way. At least that's how she saw it.

GROSS: So did she...

ROSS: We didn't mean it to be that way, you know? But she wasn't taking the jokes well, so I think everybody saw her as vulnerable and started going for it, so...

GROSS: So why was she invited? 'Cause, I mean, she's not a comic. She's not from the world of show business and entertainment. She's a political provocateur.

ROSS: I wanted her there because Rob Lowe was on "West Wing." He follows politics. He campaigns for politicians. We're weeks away from a national election here in America, and I wanted to have somebody from the political world up there to give a certain relevance to the proceedings. And she had a book coming out, and she volunteered wholeheartedly, by the way. You know, she was - seemed into it beforehand. So, Ann Coulter, if you're out there, I still love you.

GROSS: Do you mean it when you say that (laughter)?

ROSS: No.

GROSS: (Laughter) OK.

ROSS: (Laughter).

GROSS: How was the person chosen? Do they volunteer to be - does a publicist call and says, my client wants to be roasted, it will be good for his career, or do you choose them and try really hard to convince them to participate?

ROSS: (Laughter) It depends who it is. It's interesting thing. You know, I don't want to out too many people, but, for instance, Justin Bieber called Comedy Central and said, I want to be roasted. I've had a rough year. I've been arrested. I've gotten a lot of bad press. I need to reboot myself before my next album comes out. I want to be roasted. I am volunteering to be roasted. And that wound up being great for him. He had a number-one album right after that roast, and he needed the - he needed that reset button.

So they do really help the career, and sometimes it's not that tough a sell. Other times, we reach out to people. Yes, of course we've called Kanye. Of course we've called, you know, some of these more notorious figures, but they're hesitant because they don't want to be made fun of, and I get that, too.

GROSS: Some of the jokes really cut.

ROSS: I love how into this you are. I love how the minutiae of the roast has gotten into Terry Gross's head. This makes me so happy.

GROSS: Oh, I think it's kind of fascinating, I really do, 'cause the roasts are so funny and, like I said, some of the jokes are just brutal. Like, is it cheating to have writers doing the jokes as opposed to the people doing it themselves?

ROSS: It's a little bit like fantasy sports camp. You know, if you're Jewel - here's another - here's a great example. Jewel showed up a week before the Rob Lowe roast and met with the writers, and she said to my friend George Reinblatt, who's a writer on the show, she said, George, I'm a competitive person. I want to be the funniest one at the roast. And he said, we got you, Jewel.

So when somebody comes in with that attitude, we come out guns a-blazing. You don't bring a knife to a gunfight, so to speak. Jewel - nobody thought Jewel should be at a roast. No one - she was the - sort of the, you know, a surprise that she was so funny. And, yes, we load them up with writing. They put it in their own voice. They rehearse it. They can bring their own attitude towards it. Obviously, she made it hers by playing guitar through it, which was great.

And, yeah, I don't think it's unfair to have writers. I think if you're going to do a roast on television, as if you were doing a play or you were reading a script of a movie, you would have the best possible material. And those are the people who score, the people who are willing to listen to the roasting experts and then come out there and own that material.

GROSS: My guest is comic Jeff Ross. We'll talk more about roasts and how roasting became his specialty after we take a short break. I'm Terry Gross, and this is FRESH AIR.

(SOUNDBITE OF MUSIC)

GROSS: This is FRESH AIR. I'm Terry Gross. Let's get back to our interview with comic Jeff Ross, who's one of the producers of the Comedy Central celebrity roasts and has been a roaster on each one since 2005, including the roast of Rob Lowe last August. Lowe's roastmaster was David Spade. The roasters on the dais included Jeff Ross, Pete Davidson from "Saturday Night Live," singer-songwriter Jewel, the British comic Jimmy Carr and political provocateur Ann Coulter. When we left off, we were talking about how the Rob Lowe roast turned into a roast of Ann Coulter.

So when Jimmy Carr says to Ann Coulter, you could change, you could kill yourself. Is that fair? Is that an OK thing to say? I'm pretty sure I've heard other comics basically make that joke. But making it to somebody's face is - that's a rough one, especially if they're not a comic. And, you know, what did you think of that? Again...

ROSS: I love Jimmy Carr.

GROSS: ...She dishes it out. She dishes it out, so it's not...

ROSS: I understand she's - this is no wallflower we're talking about. This is not a - someone who can't take it. I thought it was funny. I can't defend someone else's jokes. I can only defend my jokes, and I have to live with my own jokes. But, you know, it was an explosive laugh. So for me to say it's not funny is - would be ridiculous. It was funny. Everybody in that room laughed, so something was happening there.

And here's the thing about comedy, Terry, and you know this. You've talking to - having talked to so many comedians over the years, it's a tough thing to analyze. As soon as you start analyzing comedy is when the world starts to fall apart, and we're second guessing it. And we are way too sensitive. Life is tough, and if we don't laugh, we're going to - our head will explode.

GROSS: You're doing roasts at an interesting time in American culture because it's a time of, like, trigger warnings, safe spaces. And every joke at one of the roasts would require a trigger warning (laughter), you know, they're - like, they're meant to be offensive in a comic way. So what's this time like for you, you know, this era of trigger warnings and safe spaces?

ROSS: It's an interesting question. You know, sometimes I worry, you know, is comedy and my type of comedy going to get stale? Is it going to be so offensive that it becomes uninteresting or so niche that I don't have an audience anymore? But it keeps getting bigger and bigger and bigger, where roasting now is a movement. These roasts are on in India, in Mexico...

GROSS: Is that right?

ROSS: ...In Australia. Not only that, they're doing their own celebrity roasts in different languages all over the world. I was just in South Africa late last year where we did a roast battle. They do these in Spanish in Mexico now. And here's the thing that makes it different, everybody I roast volunteers. Even in my live shows I'll say who wants to come up here and get speed roasted and hands go up by the dozens. Sometimes a hundred hands will go up. So to take it one step even further, Terry, more and more I'm seeing at my shows disabled people volunteering to get roasted. I had a woman in Austin get picked up, she's in a rock band called the Wheelchair Sports Camp. And her band carried her wheelchair onstage. She wanted to be normalized. There's no such thing as a normal-looking person anymore. We're all different...

GROSS: What is that - how did you roast her?

ROSS: ...And everybody understands that now. Oh, my God. Her nose ring, her tiny little body, her broken down wheelchair. She had pink hair. The fact that she was disabled was number five or six on the things that was really strange about her.

(LAUGHTER)

ROSS: So it wasn't hard at all. My best friend is disabled. There's nothing he hates more than being left out of the jokes, to be treated with kid gloves. That's the insult. People want to be part of the fun. I was down at the Comedy Cellar a couple of weeks ago and a woman volunteered to come onstage to be speed roasted. I was with my friend Dave Attell - very funny comedian.

We were up 1 o'clock in the morning, packed house, Saturday night. And this lady comes onstage, and she's kind of wobbly. And I'm thinking, oh, she's drunk. What is this going to be? And she was a 32-year-old lady wearing a bright, blue dress, and I see she's like kind of stumbling up onstage. And she gets a little closer, and I realize she has one leg. And that's why she's walking that way. So she comes onstage and she's kind of leaning on the wall and we help her up, and we talk to her. And she's a special ed teacher from the Midwest. And she's there with her husband. And we're kind of making fun of her outfit and her hairdo, and she's given it right back to us. And she's laughing so much tears are coming out of her eyes.

We finally get around to asking about her leg. And she kind of seems to want to say something about it, not shying away. She volunteered to come up there. And it turns out she is a conjoined twin who was separated as a child from her sister. So now I'm like wow, this is a really special moment. This woman has never been roasted. Her friends probably - her family they've probably been dancing around this her entire life. And now she teaches kids. It's just she's a beautiful, beautiful person inside and out.

And we finally get to the provocative part. And I say, well, you know, so you shared a leg with your sister. She's like, yeah. We're both fine. We're 32. If we make it to 36, we make the Guinness World Book of Records as the longest living separated conjoined twins. And I said, well, here's the obvious question. You know, who got the vagina?

GROSS: (Laughter).

ROSS: And she laughs and she laughs and she laughs. And she doesn't answer. And finally her husband stands up in the audience and says I did.

(LAUGHTER)

ROSS: So, you know, what's the takeaway from these moments? I am not that person. I don't know what she got out of it. All I know is it was a great moment because she came over for a picture and a hug and - after the show. And, you know, I'm not even sure what I'm doing. I'm not even sure how this helps. But when I see those smiles and I know how happy that woman was afterwards, it definitely helps me sleep better at night.

GROSS: My guest is comic Jeff Ross. We'll talk more about roasts and how roasting became his specialty after we take a short break. I'm Terry Gross, and this is FRESH AIR.

GROSS: Let's get back to my interview with Jeff Ross. He's a producer of the Comedy Central celebrity roasts and has been a roaster on each one since 2005. He's also a former board member of the Friars Club.

Why is the insult your medium?

ROSS: I don't know. You know, I wonder sometimes. I grew up in New Jersey - in Newark, N.J., and I was kind of a scrawny kid. And my dad owned a catering hall, and I would work in the kitchen. And I got - all through, you know, grade school and high school, I'd get picked on. You know, daddy's boy and, you know - but I worked really hard. And the servers were all Irish and Scottish, and the kitchen help was Jewish and Russian. The guys in the back washing dishes were all Haitian guys, and we were all sort of throwing ethnic humor at each other. We had fat and small and young and old, and I just sort of learned to dish it out and take it.

My uncle Murray - we called him mean Murray. He used to pick on me constantly, but he did it with a sort of love. I didn't get it when I was 8, 9, 10, 11 years old, but as I grew up, I realized he was toughening me up. He was giving me thick skin. And that's what you need to survive in this world. Life is tough. I've been on my own, you know - my parents passed away when I was a teenager, so I had to learn different survival techniques, I think, in comedy. You know, using comedy as a pressure release, as a release valve in life really kept my sanity.

GROSS: I don't want to ask you about your parents, but I just want to back up a second. The catering hall that your father ran, did they do weddings and bar mitzvahs?

ROSS: My great grandmother Rose - she started it a long time ago in the '50s. And then my uncles and my grandfather was the bandleader, and my dad was a cook. And my cousins were cooks, and I worked in the parking lot. I worked in the hat check. I made fruit salads. It was in Newark, N.J., and then later in Union, N.J. It was called Clinton Manor Caterers. Judy Blume wrote about it in her book "Wifey" - about it was her dream to grow up and have a big wedding at Clinton Manor. It's not there anymore, but a lot of good memories there. Yeah - weddings, bar mitzvahs, trade shows, the whole thing.

GROSS: So you must have had a taste of show business because there's always, like, entertainment at these affairs.

ROSS: I got to know the musicians because they would always come into the kitchen looking for something to eat. And I always got a kick out of that, and I would watch these weddings through the kitchen window. I was just tall enough to see through the window on the swinging doors, and my dad wore a tuxedo. And he would work the room. He was sort of the host of every party. Everybody knew him. It was a family-run business, and even though he didn't have a stage and a microphone, he was kind of the host of that show. And I think I learned a lot watching all that go down, making the customer happy, wanting everyone to leave in a good mood. It's much like the roasts. So every time I put on a nice suit or a tuxedo and do a roast, I definitely am channeling my dad.

GROSS: So you mentioned your parents. Your mother died when you were 14. Did she have cancer?

ROSS: She had leukemia.

GROSS: Then your father died when you were 19. That was sudden and unexpected.

ROSS: Yeah. He was doing stupid stuff. Drugs.

GROSS: Oh, really?

ROSS: He was a single guy, started to make some money in the '80s. He was having fun. I was away at college. My sister was a senior in high school. And, you know, he - I don't know what he did exactly. I never wanted to know. I know he did cocaine and blew his head up and he was in a coma for a few days and got to see him one last time. And then that was it.

GROSS: So when your mother died first when you were 14 and she'd been sick before dying, that must have put you in a different place than a lot of your friends because there was something tragic going on in your family for a prolonged period of time and then you were left without a mother. There was something very grave going on. And 14 is usually the age when everybody's just kind of like clowning around and - did you feel set apart by all of that?

ROSS: I knew that I was on a different trajectory. I knew that I wasn't going to have to make anybody proud in a literal way. I didn't know what I wanted to be, but I knew it was going to be different. And yeah my sister and I, we felt different. People looked at us different. There's obviously people in the world who have it much, much worse than we did. We had each other, and we had our health. And we were teenagers, and we had friends and family around.

But we did really feel like we were alone and a team. And I switched her financial aid around, and we wound up both going to college together up in Boston at Boston University so we had each other's back in that way. And we have a great bond still to this day, and, you know, I don't look at it as, you know, as you say it - the way you say it, with, you know, a sensitive way, Terry. I realize how sad it is, but at the time it just was life. I was just - I didn't know anything else. My mom had been sick for a few years, so it was a relief when she passed away.

GROSS: She knew probably at some point that she was going to die. Did she give you advice? Like, your father didn't know he was going to die when he did.

ROSS: Right.

GROSS: But your mother did. Did she give you advice about how to carry on after she was gone?

ROSS: She wrote me a sweet, sweet love letter that I got afterwards, and we would visit her at Sloan Kettering here in New York. And my dad would drive us up there, and he never fully prepared us for what was - we were going to see. And we walked in there one time and she was bald. And I don't even think I've ever thought about this 'til just now. I remember making a joke about her looking like Kojak and how she'd be able to park anywhere she wants...

GROSS: (Laughter).

ROSS: ...The way Kojak used to just pull up anywhere he wanted, and I made her laugh. We all laughed, and we cried. And we laughed. And I think that laughter is what maybe pushed me towards stand-up and writing and the things I'm doing now like wanting to hear that all the time. It was probably my last great memory of my mom was her just laughing, laughing, laughing. And so I don't know if there was any tangible, literal advice. I was so young.

But she wanted me to know how much she loved me, and she wanted me to know that she was proud of me for the way I was handling everything and taking care of my sister or at least looking after my sister. And, you know, you're a teenager. You know, everything is in your brain for a second and then you're like, all right, I got to go to football practice, I got to do my homework and I got to go - you know, but there were long nights of eating cereal and doing my own laundry and looking after myself. That really made me self-sufficient and made me strong and gave me thick skin and prepared me for life and prepared me for show business. And, you know, I think she'd like to see me settled down with a family, but we'll get there.

GROSS: So it's interesting that that joke you remember about Kojak - you were roasting your mother in the hospital.

ROSS: (Laughter) I guess so. I guess so. I never thought about that, but I think you're right.

GROSS: So you were 19 when your father died, and you had no parents then. And kids - a lot of teenagers at the age of 19 are rebelling against their parents and trying - or just trying to separate themselves and find out who they are independent of their parents. And that wasn't really going to be an issue for you because at that point, you didn't have parents. So, again, was that something that you were experiencing in a different - were you experiencing the age of 19 in a different way than your friends who were 19?

ROSS: I must have been because I remember people talking to me differently. And once you get over the mourn - the period of mourning where everybody is sympathetic and overly kind - and I hated that. You know, my neighbors offered to adopt my sister and I. And as soon as they walked away, my sister and I started cracking up (laughter). You know, there's always the gallows humor.

But once we got through that intense period of settling my dad's affairs and his business and realizing exactly what was left which was just each other. We had a bond, and I had a strength. And I had a life experience that most of my - that none of my friends had. I remember I became everybody's rabbi. Everybody who needed advice would talk to me, and it became an obvious thing. I remember my cousin - my little cousin Corinne (ph) had a boyfriend who got hit by a car and died. And she wasn't snapping out of it. She wasn't moving on. And her mom had me talk to her about loss, about death, and I realized as I was telling her that we're made to mourn and then move on.

Life has to keep going, so you can either be a victim the rest of your life and let it drag you down into drugs and alcohol and depression or you can turn it into something good, fun even, you know, and I tell young people who are going through depression that this might be the most important time of your life. This might be what makes you a great artist later on.

GROSS: So you said that because your parents were dead, you knew you didn't have to be concerned about making them proud. Did that give you a kind of permission to take chances and try comedy because you didn't have to worry about failure and disappointing your parents?

ROSS: That's a great question. I always think about that. I remember I was already doing comedy a while now and remember thinking, you know, oh, my God, I just met Buddy Hackett. I just met Don Rickles. If my dad was alive to see this, this would be the greatest day of his life. These were his heroes. He loved these guys, so it was sad, you know. And a lot of my friends - they have their parents around at their shows, and, you know, I was - just met the president and the vice president. And I was there by myself. You know, I would have had my parents there with me if they were around, so I miss them in that way.

But I would've - my - it's hard to know, but I remember very clearly in 2003 going to Iraq to entertain active duty soldiers in forward operating bases in Baghdad, Fallujah Baqubah, Tikrit. And my sister saying, you know, that if mommy and daddy were alive, you would not be going on this trip. And I think she's right, so I don't know if you can call that a silver lining or what, but I did feel liberated enough and free enough to do things that they might have stopped me from doing out of common sense and cautiousness. I went into a very dangerous situation. My hotel was mortared in Baghdad...

GROSS: Wow.

ROSS: ...And I still slept there that night because it was still the safest place to be. So I don't know, Terry. You know, it's hard to say. You know, it's been - my life and my career have been a series of happy and not so happy accidents.

GROSS: My guest is comic Jeff Ross. We'll be back after a break. This is FRESH AIR.

(SOUNDBITE OF MUSIC)

GROSS: This is FRESH AIR. My guest is comic Jeff Ross who's nicknamed the roastmaster general. He's been a roaster on every Comedy Central celebrity roast since 2005. He's also a former board member of the Friars Club. When we left off, we were talking about his parents' death when he was still a teenager.

Did the Friars Club give you a sense of belonging and family at a time when you really needed it?

ROSS: That's a great thought, and I would say absolutely. You know, the Friars Club for comedians - it's like "Cheers."

GROSS: (Laughter).

ROSS: Nobody knows your name.

GROSS: Yeah.

ROSS: Any young man I would see him walking in there in his 90s and everybody was so happy to see him, and I thought, well, that'll be me someday, hopefully. And, you know, comedians a lot of times we're on the road, we're by our self. We come home to New York to our empty one-bedroom apartment, you know, and we need a place to go where you see a bunch of other miserable people sit around and eat a corned beef sandwich. And the Friars Club really provides that, and, you know, my life is much richer now. And I don't live in that studio apartment anymore, but I still go there for the camaraderie and the way they treat and respect comedians and artists. It makes me very proud to be a comedian when I go there.

GROSS: So some of the, like, old-school comics like Buddy Hackett, Henny Youngman, Milton Berle - I mean, they could be hilarious. They could also be like incredibly sexist. And if they told a gay joke, it was going to be homophobic. So how did you deal with that being of a different generation, being more, I'm sure, aware in terms of women and gay people and racial issues than they probably were? They're from a different time. You know, what can I say? So did you find yourself having to navigate the things that you found made you really uncomfortable in addition to the things that made you really laugh a lot?

ROSS: That's an interesting question because I think I treated those comics and those kind of jokes the way you would your grandparents. Sometimes they're funny anyway. Sometimes you have to go, you know, maybe you shouldn't use that word. It'd be funnier if you said this word. It depends on...

GROSS: Would you say that to them?

ROSS: ...The timing and the...

GROSS: Would you offer...

ROSS: Oh, sure.

GROSS: ...them advice? Yeah.

ROSS: Well, but - you know what I would do - is before I had a big roast, I used to read my act, my roast to Buddy Hackett. I'd either go over his house if it was in LA and sit in the backyard and read him my jokes or I read them to him over the phone if it was in New York and he was in LA. And we sort of met in the middle. He was not like a mentor. He was more like a brother, but he was older so his sensibility would be a little different. But, you know, he was hip.

A lot of these guys, they are a lot hipper than you think. You know, sometimes they were playing to their audience and - but this wasn't the Rat Pack. I wasn't - for the most part, by the time we hit the 2000s, even the Milton Berles and Buddy Hacketts, they'd kind of came around on that sort of humor. It's very rare that an older comedian sort of slips into an old-school clunker. You know, you don't hear too much of that anymore. I think good comedy - you know, Joan Rivers is one of my heroes. She always had new, relevant material. She did not stay in the '70s and '80s with her comedy. She kept it up to date all the time, and I think that's the sort of stuff that I gravitated to. The real question is how do you stay funny in your 70s and 80s? And that's a real accomplishment, you know, the longevity. Comics just don't retire. They either die young or they go to 100.

GROSS: Jeff Ross, it's been great to talk with you. Thank you so much.

ROSS: This is so fun. Terry Gross, FRESH AIR - I feel like I made it.

GROSS: My interview with Jeff Ross was recorded in September. A new round of his Comedy Central series "Roast Battle" began last night.

And that concludes our series featuring some of our favorite interviews of 2016. Tomorrow, when we return to new interviews, my guests will be Lin-Manuel Miranda who wrote and originally starred in the Broadway hip-hop sensation "Hamilton." He wrote several songs for the new Disney animated movie "Moana." We'll have plenty to talk about. I hope you'll join us.

(SOUNDBITE OF SONG, "MY SHOT")

LIN-MANUEL MIRANDA: (Rapping) I am not throwing away my shot. I am not throwing away my shot. Hey yo, I'm just like my country. I'm young, scrappy and hungry. And I'm not throwing away my shot. I'ma get a scholarship to King's College. I probably shouldn't brag, but dag, I amaze and astonish. The problem is I got a lot of brains but no polish. I got to holler just to be heard. With every word, I drop knowledge. I'm a diamond in the rough, a shiny piece of coal trying to reach my goal. My power of speech...

GROSS: FRESH AIR's executive producer is Danny Miller. Our technical director and engineer is Audrey Bentham. Our associate producer for online media is Molly Seavy-Nesper. Therese Madden directed today's show. I'm Terry Gross. All of us at FRESH AIR wish you a healthy and fulfilling 2017.

(SOUNDBITE OF SONG, "MY SHOT")

MIRANDA: (Rapping) I am the A-L-E-X-A-N-D-E-R. We are meant to be a colony that runs independently. Meanwhile Britain keeps messing with us endlessly. Essentially, they tax us relentlessly. Then King George turns around, runs a spending spree. He ain't never going to set his descendants free, so there will be a revolution in this century. Enter me.

UNIDENTIFIED SINGERS: (Rapping) He says in parenthesis.

MIRANDA: (Rapping) Don't be shocked when your history book mentions me. I will lay down my life if it sets us free, Eventually you will see my ascendancy. And I am not throwing away my shot. I am not throwing away my shot. Hey yo, I'm just like my country. I'm young, scrappy and hungry. And I'm not throwing away my shot. Transcript provided by NPR, Copyright NPR.