In the predawn hours of a late Nevada night, two comedians cannot bring themselves to leave a Las Vegas coffee shop. Long after their meal, as 4 a.m. turns to 5 following a festival performance at the Caesars Palace, they are either too tired, too stoned or too happy to get up and conclude the evening.
Jeff Ross and Dave Chappelle had known each other for more than a decade, comics who helped trace one another’s rise to fame through the New York comedy scene in the 1990s. They had spent untold hours together and held almost every intimate conversation two close friends with the same job could have, though on that night in 2005 there was much more to say.
Ross had grown in some way distraught. His career was a success, a renowned stand-up and Friars Club comic enjoying a new level of celebrity through his water-cooler sets at Comedy Central’s roasts. His jokes were vicious, delightful, legendary. At the roast of Jerry Stiller, in 1999, after a particularly uncomfortable act by Sandra Bernhard, Ross remarked, “Sandra Bernhard: I wouldn’t fuck you with Bea Arthur’s dick.” At the roast of Pamela Anderson, in 2005, Ross turned to the dais and offered, “How is it possible that Courtney Love looks worse than Kurt Cobain?”
The lines killed, the kind of landmark jokes that would fight for space on any comic’s tombstone, but Ross wasn’t so sure about what they had come to represent. When he first began roasting, in 1995, he was in total wonder. “It felt like walking into my Yankee Stadium,” Ross, 51, says today. “Like, Wow, this is the kind of comedy I think I might have to be doing.” Yet as time passed, such a fixture had Ross become at these events that he was beginning to be known only as the Roast Guy. His customary appearance on Comedy Central opened him to ridicule from other comics, who cracked at the podium that he could not find better gigs. Even to Ross, who later wrote that he holds a “black belt in busting balls,” the jokes hurt.
In the coffee shop, a young comic from Boston approached, seeking advice from Ross and Chappelle on his fledgling career. Chappelle placed his hand on the kid’s arm and said, “Don’t worry. You only start out once.” Relieved, the young comic walked off, though his presence sparked a lament about Ross’ own place in comedy. Where is this going? he wondered. Being an expert on roasting is like saying I’m into fencing or Latin. It’s kind of a lost art. Am I really going to be a fringe player in my own industry?
But Chappelle wouldn’t hear it. Too long, as his own career began to skyrocket into comedy’s highest stratosphere, had he been Ross’ cheerleader. In April 1995, when Chappelle appeared on the Late Show with David Letterman and Ross could not seem to earn his own booking, it was Chappelle’s urging to the show’s producers that finally landed Ross on stage nine days later. “Dave had faith in me before I did,” Ross says. “He’d been in my corner before I even understood what that meant.”
On that night in Vegas, Chappelle refocused his troubled friend. “That’s your lane, dude,” he said across the table. “People dream about having something they’re known for and something that they’re the best at. Expand that lane, take it all the way and make roasting cool.”
The moment may be the genesis of the Roastmaster General, the nickname and persona Ross has since wholly embraced. It may be where it all truly began—the explosion in popularity of roast comedy, the true appreciation of the art and its restorative properties, the time Charlie Sheen and Justin Bieber called Comedy Central and volunteered to be roasted. Their reputations were in such shambles that only placing themselves in front of a comedian firing squad, showing they were good sports and that they could take a joke, could repair the damage.
At the crest of it all has been Ross, the most audacious roaster there has ever been, who can dress like Muammar Gaddafi at a time when the Libyan tyrant is still on the run, who can report to Donald Trump, then considering a run for president, that he “can’t wait for the assassina—I mean, the inauguration,” who can even lampoon Texas inmates and Boston cops to their faces and still win their regard when the set is over.
Suddenly, what Chappelle once called his lane is so much more. It is a near-annual event. It is a TV show. To Ross, roasting is a movement. “Now, I feel like my lane is a turnpike,” he says. “It’s a six-lane highway, where almost anything is possible.
"I realized I have the coolest fucking job in the world.”
Jeff Ross was raised in New Jersey, which is itself a birthright to bust chops, but he learned how to give and take a joke working in the sweaty kitchens of his family’s catering company just outside Newark. His father, Ronny, ran the business, and so Ross was known as the boss’ son, an easy mark for staff to pick on.
He would get chirped for having red fingernails from placing maraschino cherries atop thousands of fruit cups every weekend. “There were drinking jokes and fat jokes,” Ross recalls. “It was a free-for-all, and a way to get through a very high-stress, high-pressure gig.”
At a young age, Ross began to dole it out, too. Yet some of his earliest joke memories are also some of the most tender times of his life. At 14, his mother, Marsha, was dying from leukemia, and Ross, his sister Robyn and his father went to visit her as she lay inside New York’s Memorial Sloan Kettering hospital. It was a devastating scene, Marsha’s treatments having ravaged her, and to Ross there was one way to change the mood of the room. He began to riff on his mother’s newfound baldness, likening her to Kojak, the title character of the ‘70s cop show. Ross watched Marsha come to life, the smile return to her face.
They left the hospital that day and stopped on 7th Ave., at the Carnegie Deli, on the way home to New Jersey. “What I remember from that, and I don’t think I’ve ever thought about this before, is afterwards laughing at the jokes with my sister and my dad over a miserable sandwich,” Ross says. “And that was a way to talk about the experience without talking about the worst parts of the experience. It was like a happy memory of a sad thing. If we don’t laugh, we cry. And who the fuck wants to cry?”
The time by his mother’s bedside may have been, if you hold it up and look just right, Ross’ first roast. The therapeutic powers of the laughs he shared that day with his family were not lost on him. He learned the allure of the roast joke, that a wisecrack, told with the right amount of respect and reverence, could be a magical thing.
‘You take one look at Jeff and you know there’s not a mean bone in his body,’ Kimmel says. ‘I don’t think there are any bones in his body.’
Ross rose as a comic in New York, where he was adopted into the Friars Club, the hallowed ground of comedy’s most sacred names: Milton Berle, Henny Youngman, Buddy Hackett. He found the roasts and excelled, burning old showbiz names like Abe Vigoda and Alan King. It was Ross who had a leading hand in bringing the roasts out of the closed banquet halls of the Friars Club and into the light, where, beginning in 1998 at the roast of Drew Carey, they were first broadcast nationally on Comedy Central.
Hollywood found him in other ways—Jimmy Kimmel hired Ross as a writer on The Man Show; Ross fed punchlines to the monologue of Billy Crystal at the Oscars in 2000; much later, in 2008, Ross appeared on Dancing with the Stars—but roasting was always his finest craft. As Comedy Central honored celebs like Anderson, William Shatner, David Hasselhoff and Flavor Flav, Ross in many ways stole each show, his sets bulldozing targets and doubling over audiences.
Which made it all the more peculiar to Chappelle and Ross’ other friends in comedy that he was having second thoughts about his place as the Roastmaster General. “I think it’s in the same way that Michael Jordan didn’t want to be pigeonholed as a basketball player,” cracks Kimmel. “If you have one thing you’re great at, you’re great at that one thing. I don’t anticipate many feature film roles coming my way. I’ve been pigeonholed as a talk show host, and I’m perfectly fine with that.”
It was only a matter of time before Ross began to really strut his roasting feathers, provoking audiences at each performance with outfits as outrageous as his one-liners. During the height of the Penn State sexual assault scandal, Ross roasted Roseanne Barr dressed as the late football coach Joe Paterno. He roasted Sheen as Gaddafi, Rob Lowe as Prince. He roasted James Franco wearing cornrows and a neck tattoo, a nod to Franco’s infamous character in the movie Spring Breakers. Don Rickles, the venerable old insult comic, poked fun at Ross for his garish ensembles. “Every time you do a roast,” he told Ross, “it’s Jewish Halloween.”
He grew more comfortable on stage, his jokes just as pointed but his delivery more relaxed, more affable. Ross could obliterate a target, like friend Sarah Silverman, and make them swoon in the same moment: “I’m so proud of you, Sarah, for your success in the animated movie. Anybody see Wreck-it Ralph? Which is what guys do to your pussy. They wreck it, then they ralph.”
This, in a sense, is Ross’ greatest trick: never hold back on a joke but layer it with a genuine affection for the roasted, and he can get away with murder. “I think people tend to not be hurt because the craft of a joke by a comic of Jeff’s unique caliber is not just about the words,” Silverman says. “It’s the contrast of the words with the warmth and kindness and love and even respect that transcends through him and the words he’s saying.”
“There’s some kind of unquantifiable chemistry that some people have,” says Kimmel. “I think people get a sense of that. Jeff is not exactly Brad Pitt, so when he’s making fun of someone’s appearance that pill is a lot easier to swallow.”
The late-night host became excited at the chance to dig at the looks and waistline of Ross, who has chafed on Kimmel so often over their long friendship—at Kimmel’s house each year on Christmas Eve, for instance, or at Kimmel’s 2013 bachelor party in Vancouver, where Ross’ impromptu roast at a Chinese restaurant was so disruptive Kimmel was certain their food would arrive at the table bathed in spit.
But through every barb, Kimmel has never questioned Ross’ intent. “You take one look at Jeff, and you instantly know there’s not a mean bone in his body,” Kimmel says. “I don’t think there are any bones in his body.”
Ross has always seen in roasting an opportunity. For those willing to volunteer to be honored, it was if something miraculous happened. The roasting humanized them, Ross held, it made them vulnerable. No matter their transgressions, the roasting made them likeable again.
So it was that in 2011, Sheen, fresh off a drug-fuelled, public meltdown in the wake of his dismissal from Two and a Half Men, contacted Comedy Central about being roasted. (Ross: “You make your own father ashamed that he shares the same fake name as you.”) Later, in 2015, Bieber, his reputation flagging following a number of arrests and high-profile faux pas, did the same. (Ross: “Lately a lot of people have been pointing their fingers at you. And those are just lesbians showing the barber how they want their hair cut.”)
The shows were cleansing. Ross observed that the experience was “therapeutic” for Bieber, who, like Sheen—who was cast as the lead in a new sitcom following his roast—was recharged in the public eye after allowing himself to be the butt of so many jokes. “Honestly, I didn’t give a shit about Justin’s music and his exploits until the roast,” says Ross. “And then I got to know him and I got to like him.”
The pop star’s management was so grateful for Ross’ role in his rebirth that it sent backstage passes for Ross and fellow Bieber roaster, Pete Davidson of Saturday Night Live, to a recent concert. “It was amazing,” says Ross. “In fact, I got my period for the first time during that show.”
Amid all the crass jokes, Comedy Central’s roasts took on a kindness to them, a feeling of family members ribbing one another at a private wedding reception. In large part, that was a credit to Ross. “Any humanity in those things,” says Silverman, “are because of Jeff.”
One of my best friends is disabled, and there’s nothing he hates more than when we leave him out of the jokes.
Ross wanted everyone to enjoy themselves at the roasts, and he walked the walk: when Jersey Shore castmate Mike “The Situation” Sorrentino began to bomb at the roast of Trump, in 2011, Ross approached the podium and placed his arm around the reality star, pleading with the hissing crowd to give him a chance. When conservative firebrand Ann Coulter was being torn apart at last year’s Rob Lowe roast, there was Ross, absurdly outfitted in a purple Prince suit, turning to Coulter with an encouraging smile, goading her into loosening up and trying to roll with the haymakers being thrown her way.
“He’s just about everybody having a good time, and it’s really not about hogging the stage or really stealing anyone’s light,” says Amy Schumer, who shot to prominence, in part, through her sets on Comedy Central roasting Sheen and Roseanne. “He’s really about, 'There’s room for all of us.’”
He had mastered the art of the roast, but the question next for Ross was what else he could do with the medium. He felt emboldened, having rounded into his prime years as a comic, but his ambitions were crowning higher, too. Ross wondered if he couldn’t make real social change with his roasting. He had long performed for the military in outposts like Iraq, Afghanistan and Guantanamo Bay, and he began to roast those troops who volunteered to be razzed upon. In places so serious and tense and starved for comic relief, Ross noticed it brought an outsized sense of joy to his shows.
In 2015, he embarked on his boldest roast quest to date for Comedy Central, riffing on hardened criminals inside Texas’ Brazos County Jail. Then, as tensions roiled between cops and civilians amid a host of fatal police shootings caught on camera, Ross roasted officers of the Boston Police Department last year in a one-hour special. At each show, he found a segment of the population—convicted felons who might one day be released again into society; cops trying to recapture the public trust—in need of image rehabilitation. Ross felt he could roast them back to humanity.
It was roasting as social experiment, and whether it moved the needle any or not Ross has other aims. The homeless, the handicapped—these are people Ross feels can still benefit by being normalized through comedy. “One of my best friends from when I grew up is disabled, and there’s nothing he hates more than when we leave him out of the jokes,” Ross says. “That’s the ultimate insult, to be ignored or skipped over because you look different or walk different or sound different.”
His theory has held weight in Roast Battle, Ross’ comedian vs. comedian insult show on Comedy Central, which will air the series’ Season 2 finale Sunday night. Several contestants on Roast Battle have been in wheelchairs, disabled or disfigured. They were the brunt of brutal jokes from other comedians, but they told brutal jokes of their own, too.
“They’re just as funny or funnier than pretty people,” Ross says. “Comedy is not just for the cute anymore.”
There is a dream list in Jeff Ross’ head. He’d love to one day roast Kanye West, or Bill Clinton or his pal Kimmel, or even Barack Obama, a civilian now and ripe for the picking.
It is something of a contradiction of terms that Ross can go on like this, prodding and poking at people without casting himself down a river. And yet the opposite appears true. He is beloved, especially among fellow comics, who say Ross is as charitable working to advance their careers as he might be his own.
As she was beginning in show business, Ross would host Schumer in his guest house when she was broke and without the money for a place to stay in L.A. “This is what a man would call a guest house and a woman would call a shed with a space heater,” she jokes, but the gesture is no less lost on Schumer, who has been counselled by Ross at many turns on her way to the top of the comedy A-list. “I’m not done getting advice from Jeff,” she says.
It is a generosity Ross feels he owes back to comedy, much in the spirit of the older comics who took him into the Friars Club all those years ago. To Ross, it’s a responsibility. In comedy, there is honor among thieves.
On, then, he roasts, his Roast Battle the latest extension of Ross’ thesis that there is healing power in being able to take a joke. During one episode of the show’s first season, the actor Steve Rannazzisi appeared as a contestant. Rannazzisi, a star of FX’s fantasy-football comedy The League, had suffered a tremendous blow to his public reputation in 2015, when he admitted in the New York Times that he had lied about escaping the falling World Trade Centers on 9/11.
The disgrace seemed to overshadow his career when, last year, Rannazzisi decided he would appear on Roast Battle. He knew he’d be killed, understood his presence would be like fresh meat to a roving pack of hungry comedians, yet he went ahead as a contestant, anyway. “To me,” Rannazzisi says, “it was like, I’m going on the show to let everyone have their licks and just get it out and put it past me.” He was crushed, of course, but there he was after the episode taped, with his fellow comics at the Hyatt hotel bar in downtown Montreal, almost with a new lease on life. He cheerfully told Ross, “I can be friends with everybody again.”
Hours earlier at the show, before he had been baptized by “Roast Battle” and cleansed of his proverbial sins, Rannazzisi readied himself on stage. Ross, acting as a judge to the upcoming competition, calling upon what Kimmel marvels as an ever-updating library of jokes in his head, volleyed about his own jabs toward his actor friend. “Steve, you look a little nervous. Are you OK?” Ross asked. “Let’s hope you didn’t also lie about being a comedian.”
The crowd roared, and Rannazzisi could only smile, stand and take it. It was vicious. It was delightful. Coming from Ross, it was an honor.
“Who else,” Rannazzisi says, “would you rather get roasted by?”