Like many sketches on The Late Show with Stephen Colbert, it plays off news from the White House — in this case, recent stories about adult film actress Stormy Daniels’s tryst with Donald Trump before he was president. After Daniels had revealed how Trump had expressed hatred for sharks, increased donations flowed to shark conservation groups.

That led to the mock infomercial that opened the show that night. Accompanied by a guitar-playing shark, Stack, as the straight-laced CEO Burt Ridgewood, explains the benefits of putting live sharks into used cars, despite the high probability that drivers would be eaten in traffic.

The punchline features a picture of Stack, smiling, dressed as a double cheeseburger.

“It was so ridiculous,” Stack says. “One of my favorite compliments is when someone tells me: ‘That’s so stupid.’ That’s often my most favorite stuff — when it’s wonderfully dumb.”

Since the late 1990s, Stack has thrived by writing and performing wonderfully dumb sketches with some of late-night television’s biggest stars. After writing for Conan O’Brien’s show for 17 years, he joined the Colbert production team on CBS in 2015.

On O’Brien’s show, Stack had indulged his inner clown, writing for one of television’s funniest comics. But with Colbert, whom he’d known from their days in Chicago with the Second City improv troupe, Stack had to recalibrate his approach. Colbert’s forte is comic commentary on the day’s news. In a media landscape where satire has found a strong footing on television, Stack moved his antic, wacky humor into the political arena.

“It’s a challenge to funnel my natural … non-topical brain into the world of politics,” Stack says. “With Conan, we would address the news in a glancing, silly way. It was like fun cartoons. It never felt as driven by the news as our show feels at Colbert these days.”

That focus has added a certain immediacy to the joke-making process, especially with a president whose Twitter blasts provide ample fodder.

“There’s such a fast turnaround,” Stack says. “Sometimes we’re doing rewrite until showtime, but when it’s 5:30 p.m., that’s the script. You want it to be as good as it can be, and you also have to let it go. There’s always a show tomorrow.”

Get Me Rewrite

Making jokes for the Late Show starts early each morning after Stack’s commute into Manhattan from his home in Sleepy Hollow, about 25 miles north of New York City, to his office at the Ed Sullivan Theater on Broadway. He and members of the writing staff toss around possible bits for Colbert’s monologue or “cold open” skits like the zany shark piece.

Stack’s improv skills come in handy during the collaborative writing sessions, where he and his colleagues build on each other’s ideas, even if what’s suggested doesn’t turn out to be all that funny.

“A bad idea can lead to a good one,” says Stack. “You need to feel free to toss out one that might be bad. That’s healthy brainstorming.”

Colbert is very much involved in the process. “He’s as much a writer as a host,” says Stack. “He’ll riff around in the rehearsal, tweak the language, or flat-out write new jokes on the fly.”

Those riffs can also occur when Colbert and Stack converse on camera, as when Colbert looks heavenward to speak with God, the animated character whose mouth moves to Stack’s voice-over. In one February sketch, Colbert asks God about the NRA president’s contention that gun ownership was a right granted from on high.

Colbert wonders if God is pro-gun.

“You created the Second Amendment,” God retorts. “I said a ‘well-regulated militia.’ That doesn’t sound like buying an AR–15 should be easier than buying Sudafed.”

Even on camera, Stack thrives on such nail-biting spontaneity. “I like it when we go off on riffs — when you go off the rails and know you won’t be left hanging,” he says. “That can be the most fun.”

Chunkable Comedy

At 53, Stack is tall and lanky, with a full head of red hair that can be slicked back and neatly combed on air. It’s somewhat untamed when he shows up to speak in late October at the Hudson Valley Writers Center in Sleepy Hollow, not far from his home. He’s around the same age as O’Brien and Colbert, part of the late 1980s and early 1990s generation that found inspiration in Chicago during what Stack likes to call the golden age for improv comedy, when he found his comedic voice alongside future stars Colbert, Steve Carell, Amy Poehler, and Tina Fey. Dressed in a gray button-down shirt with gray slacks and black suit jacket, he talks about how Americans may not stay up until midnight to watch his latest sketches. But many of his fans watch regularly on short clips that run a minute or two and get shared on Facebook or Twitter.

“People watch TV today in chunks,” he says. “You hope that you make something that’s chunkable, something that’s shareable.”

Colbert’s writing staff includes a slew of young writers, whom Stack says he relies on at times to keep himself up to date.

“I’ve been married since 1996, so certain areas of social media, like Snapchat and Tinder, which enter into scripts at times, are alien to me,” he says. “I sometimes worry about my references. But I’m pleasantly made aware every day that we are almost always on the same page. I relate so much to their sense of humor and what they find funny.”

That’s not to say that Stack shuns social media. He has more than 33,000 Twitter followers at @BrianStack153. A recent header photo depicted him in a goatee, mustache, and glasses, intently reading a volume titled Things Only Weenies Care About.

His feed is, as befits a comedian, hilarious — and sometimes moving. In a tribute to the late Anthony Bourdain, who tragically took his own life, Stack reveals that he has also had a brush with depression. He comments on movies, politics, and musicians ranging from Prince to John Prine. And he retweets other comedians and hysterical dog videos — including his own. There’s his dog, Darby, tailgating in a Badgers hat before the Orange Bowl, resting his head on a pillow while his master shovels snow, and lying inside the front door covered with mail because he was “too lazy to get up when the mail was dropped on him through the door slot.”

The Ark of His Career

Stack’s comedic journey began at the Ark Theatre in Madison, located in a converted garage on Bassett Street. A graduate of Indiana University, Stack had taken a comedy improvisation workshop in Chicago in the summer of 1986. He arrived in Madison that fall to pursue a master’s in communication arts, delving into the psychology of media and contemplating a career in academia or advertising.

In Madison, he mustered up the courage to audition at the Ark to give comedy a shot while hitting the books for his graduate studies.

“I was so scared to try,” says Stack. “Once I did it, I wished I’d done it earlier.”

Among those in the company were up-and-coming comic Chris Farley and longtime Onion writer Todd Hanson x’90.

“I connected right away with Chris, even though we didn’t seem to have anything in common,” recalls Stack. “He was a big guy from Madison. I was a skinny, unathletic kid. We bonded through comedy. Chris couldn’t wait to get to Chicago, and by 1990, he was in New York on Saturday Night Live. I went to see his first show. I didn’t expect to know someone on television.”

At the time, Stack couldn’t imagine a way to make money making people laugh. After graduation, he moved back home to Chicago to work for four years in an ad agency. But comedy still beckoned, so he performed improv for fun on weekends.

He was really funny. Maybe he could follow Farley’s path to the big stage, he thought. “While I always dreamed of having some kind of career in comedy, I never thought that seemed realistic at all, since [I thought that] show biz people came from another planet,” he says. “I really didn’t have any idea what ‘realistic’ career to pursue while doing improv for fun early on.”

That became a moot point after he landed a job with the touring company of Second City. Comedy led to romance, too. He met his wife, Miriam Tolan, in a Chicago improv ensemble called Jazz Freddy. They worked together at Second City, got married, and have two daughters, Nora, 20, and Colette, 16.

“The friendships and relationships formed through improv become so strong,” he says. “You are in the trenches together, relying on each other. It feels like you are going into battle together. You have each other’s backs. And back then, after the shows, there was socializing — way too much partying during those Chicago days.”

After four years at Second City, Stack had his big break, joining the writing staff at Late Night with Conan O’Brien for what was to be a 13-week stint. A sketch he wrote for Amy Poehler, with her playing a 13-year-old, helped convince the powers at NBC to extend his contract. His fill-in gig turned into 12 years with O’Brien’s show on NBC, and another five years after O’Brien moved to TBS.

It was a run that led to five Writers Guild Awards for Writing in a Comedy/Variety Series and an Emmy award in 2007.

That first year on Late Night wasn’t easy. Stack recalls the December day that O’Brien walked grim-faced into the writers’ room. He told them that Chris Farley was dead, at age 33.

“It was really hard,” says Stack. “I’d been so excited for Chris when he made it to Saturday Night Live, but also worried for him. He was childlike in his vulnerability. He was fragile and easily wounded. He had so much life in him. I couldn’t believe you could snuff that out.”

Although Stack’s sense of loss has lingered to this day, he continued to hone the sense of comedy that has landed him on late-night’s most highly rated talk show.

Late-Night Badgers

Stack isn’t the only Badger contributing to Colbert’s signature brand of laughs. Gabe Gronli ’04 and Aaron Cohen ’03, who had worked as interns with Stack at Late Night with Conan O’Brien, moved to CBS to join the writing staff with Stack when The Late Show with Stephen Colbert debuted in 2015. Cohen, now a writer and supervising producer for Colbert’s show, marvels at Stack’s range.

“There are very few people who can play both God and the devil,” he says. “When Stack plays God, he’s a bumbling, lovable God, and his full, red-body-painted devil is just as likable.”

Gronli, one of the Late Show’s writers, grew up on Madison’s west side. He remembers the first day of his Conan internship, when he met Stack, whom he calls the friendliest person he’s met during his television career.

“I was an avid Conan fan, and Stack was an idol of mine,” says Gronli, a founding member of Madison’s Atlas Improv Company. “He’d heard about me and greeted me by name when I came out of the elevator. I was so happy. Brian Stack knew my name!”

Gronli says Stack has an uncanny ability to create characters, each with a distinct point of view and mannerisms to match. This all comes out in the collaborative writing process, which Gronli says occasionally circles back to Madison.

“When working with him, he’ll go from something incredibly funny, to coming up with a great character, to shouting about old restaurants in Madison he’s eaten at, to his favorite rock band,” Gronli says. “He has a unique brain for characters. He inhabits them very easily.”

Stack believes that his knack for writing emanates from his training in improv, which he still performs monthly in Manhattan at the Upright Citizens Brigade show Gravid Water. The show features experienced stage actors who recite lines from a play, with the improvisor, who hasn’t read the script, responding to lines they’ve heard for the first time. In late February, Stack adopts a deadpan British accent in a scene from the play Mary Page Marlowe. It’s a scene in which a husband faces allegations of infidelity from his wife.

Stack’s character brushes off the allegations, but his disinterest in the marriage is revealed. The audience erupts in laughter after Stack tells his estranged wife that he’ll watch over their baby — whose name he can’t remember.

“It’s a way to keep my chops up,” says Stack. “Improv is my first love. It keeps your synapses firing.”

Larry Busacca/Getty Images

Anders Holm ’03 was in New Orleans when he got a call from his manager about a job opportunity. The following day, sitting in his hotel room, Holm auditioned for The Intern via Skype. Hours later, he was on a flight to New York City to meet with the movie’s director, Nancy Meyers, and its stars, Anne Hathaway and Robert De Niro.

And that, as Holm puts it, “was that.” He nailed the audition and landed the job.

Garnering a starring role opposite megastars in a Warner Brothers romantic comedy is just the latest career triumph for Holm, who grew up in Evanston, Illinois. Since moving to Los Angeles twelve years ago, he’s made a name for himself in a town known for its cutthroat mentality.

Holm’s real-life Cinderella story began five years ago when Comedy Central greenlit Workaholics, a series the thirty-four-year-old co-created, produced, and wrote with Blake Anderson, Adam Devine, and Kyle Newacheck. The single-camera comedy centers around three slackers (played by Holm, Anderson, and Devine) who “work” at a telemarketing company during the day and party at night. The underachieving trio proved an instant hit with viewers.

The show and its go-getter stars also caught the attention of Hollywood.

Since the 2011 debut of Workaholics, Holm landed a recurring part in Mindy Kaling’s television series The Mindy Project, as well as a slew of highly coveted small roles in major Hollywood films, including Inherent Vice, The Interview, and Top Five. And while Holm is best known for his improv and absurd comedy, he earned unexpected praise at 2015’s Sundance Film Festival for his dramatic acting chops in Unexpected, an independent film about an unlikely friendship.

The writer-actor closed out 2015 on a high note both personally and professionally. In December, Holm and his college-sweetheart-turned-wife, Emma Nesper ’04, celebrated their son’s second birthday. That was preceded by The Intern’s splashy Manhattan premiere; news that Comedy Central extended Workaholics for a sixth and seventh season; winning yet another noteworthy role in a Hollywood romantic comedy, How to Be Single, starring Rebel Wilson and Dakota Johnson; and being chosen to write a screenplay for a project that he’s developing with Seth Rogen.

But Holm is quick to point out that while his rise in the entertainment industry came quickly, it certainly didn’t happen overnight. His big breaks in both television and film required the Roman philosopher Seneca’s recipe for luck — loads of preparation paired with opportunity.

Holm returned to campus to speak at commencement in spring 2013, when he told graduates, “Be prepared to work harder than anybody else for what you want. … but always take time to watch cartoons.” Bryce Richter

Holm’s preparation began during his college years at UW–Madison, where he was a member of the varsity swim team and majored in history. In between the 50-meter freestyle, homework, and hanging out with friends at the Essen Haus, Holm wrote screenplays. A lot of screenplays.

“I’d go out on Thursdays and Fridays, and then stay in on the weekends to write,” he says. “None of the scripts I wrote in college were that good, but at that point, it didn’t matter. I was just trying to just write as much as I could.”

The effort paid off. One year after graduation and nine months after moving to Los Angeles, Holm landed an internship at power producer Barry Josephson’s Josephson Entertainment. That led to a meeting with Bones creator Hart Hanson, who, after looking at some of Holm’s screenplays, hired him as a writer’s assistant. It was while working on Bones that the actor had a revelation.

“When I moved to LA, I wanted to be a writer and write movies,” Holm explains. “What I didn’t know then is that you write the movie, you sell the screenplay, and usually it’s out of your control. It could be rewritten or changed significantly. So it’s no longer yours. You just hope for the best. But in television, the writers hold a lot of creative control. If you create a TV show as a writer, then you are in control. You’re the auteur. So I quickly learned that my ego was better suited for TV.”

During this time, Holm also learned that he didn’t exactly enjoy being an assistant. “I’m just not very good at getting lunches,” he says. “Dealing with somebody who can’t handle that their favorite soup isn’t available is frustrating. But I never got too down about it, because when I moved to Hollywood, I was naïve and confident enough to [tell myself], ‘You’re going to be making money in this town for your writing.’ The problem was I never knew how it was going to come to me. So I got by with the help of my then-girlfriend, now-wife [Nesper], and doing the classic charge-everything-to-the-Visa. I told myself that I’d pay it off when I ‘made it.’ It definitely wasn’t the safest bet, but I decided to bet on myself.”

While Holm never planned on becoming an actor, he soon found out that as a comedy writer, the quickest way to prove to people that his words were funny was to perform his own material. In 2005, right before starting a job as an assistant on HBO’s Real Time with Bill Maher, Holm met his soon-to-be Workaholics co-stars Devine and Anderson while performing at the renowned sketch-comedy group Second City LA. In 2006, the trio, along with Kyle Newacheck, formed Mail Order Comedy — a group devoted to writing material, performing at various venues, and filming their own skits, which they uploaded to YouTube. Cut to 2011. After viewing their online content, an executive at Comedy Central approached the group to make a pilot. While Holm considers that call a highlight in his career, he doesn’t regard it as his “I made it” moment. That came a few months later, when Comedy Central ordered a second season of Workaholics before season one had even aired.

“It’s such a timing thing that comes into play with Hollywood,” Holm admits. “There is no ladder in the business of entertainment. You can’t just put in hard work and work your way up. Out here, it’s more like you can do no work and get a big break in two weeks, or you can work hard for ten years and never catch a break. So it’s kind of a crapshoot.”

While betting on himself paid off for Holm, he still experiences moments of insecurity about his career. “When I was shooting The Intern, I would look at Anne Hathaway and Robert De Niro and think, ‘I come from the land of fart jokes.’ So I started to think to myself, ‘All right. Who really thinks I should be here?’ But then, by day two [of shooting], it wasn’t as wild as I thought it might be. And listen, it’s amateur to not think you should be there. You have to show up and do your job and have the confidence.”