From late-night TV to YouTube and live improv circuits, Tigers risk everything for comedy
words by Jeremy Gerlach
illustrations by Katy Freeman ’17
photos provided by featured alumni
Comedian Raj Desai ’99 has busted the guts of D.C. journalists, late-night audiences, and couch-ridden 20-somethings glued to their Hulu accounts, but one of the toughest crowds he ever faced was in his parents’ living room.
In 2005, the Trinity biochemistry major—who also has a George Washington University law degree—stood in front of his mother and father in their Arlington, Texas, home, explaining to them why he was walking away from a career in civil litigation: He wanted to move to Los Angeles to become a standup comedian.
“I wouldn’t say they were glad about what I was doing with my life,” Desai deadpans. “But they at least didn’t stop me.”
Jump forward 13 years, and it’s safe to say Desai has won over his audience. He’s a successful comedian who’s landed absolute zingers for Anthony Jeselnik, Triumph the Insult Comic Dog, and the 2017 White House Correspondents’ Dinner, and now writes on Sarah Silverman’s I Love You, America—rated 93 percent on Rotten Tomatoes.
And Desai isn’t the only Tiger holding a feather to America’s collective ribcage. Trinity has a long list of alumni who’ve become standups, writers, and even founders of improv groups. They span TV, streaming networks, and live performance circuits. Some are pros who spend more than 12 hours daily writing jokes that will echo worldwide, while others perform for free on the weekends for the sheer joy of the experience, grinding in between work shifts to craft intimate connections with small, local audiences who’ll never hear the same joke twice.
For all of these Tigers, comedy is a risk. For some, it’s existential: If your jokes don’t land, the bills don’t get paid. For others, it’s borderline-spiritual: If a live show rocks, the endorphins flow.
And at Trinity, we know you don’t bring down the house by playing it safe.
Desai has traded in the oak trees of Trinity’s campus for the lush palms of Hollywood. How’d he get here, you ask? Well, every morning, he swings down sunny Santa Monica Boulevard and onto the lot at Sunset Las Palmas Studios, home to the I Love You, America set.
But if you’re looking for an answer Google Maps can’t show you, Desai has seemingly always had this destination entered into his spiritual GPS.
“I would say since I was a young kid, really, like 12, I was obsessed with standup comedy and comedy in general,” Desai says. “One of the most important things to me at Trinity was watching Late Night with Conan O’Brien every night at 12:30 on NBC in my dorm. We didn’t have DVR, so I either had to stay up and watch it or VHS-tape it and watch the next day.”
And while swamped in law school, Desai always made time for LexisNexis searches on famous comedians and writers, prying for clues about how they launched comedy careers. (Our Gen Z readers should note three things: LexisNexis was the Google of its day; VHS is how humans used to watch movies; and no, this story will not also run on the History Channel between Mysteries of the Ice Age and Coleen Grissom: the Younger Years.)
“My assumption was that everybody who works in showbiz, like, their dad was the ‘President of Showbiz’ or something,” Desai says. “But I just started reading about Conan O’Brien and Jon Stewart and others, and I kind of figured out how most people got into comedy writing and stand up: They just packed up their car and moved to L.A. or New York, got a day job, and started doing it at open mic nights.”
So Desai took a risk: He loaded up his ’94 Camry and headed to L.A. There, he went from “sort of a total zero” to the top of the “minor leagues of stand-up” relatively quickly, eventually pulling enough of his own showbiz weight to attract an agent and manager. He made appearances on programming such as The Late Show with Craig Ferguson and Comedy Central, and then, after some rough, “lean years,” he got writing gigs on shows such as The Jeselnik Offensive. Stints with Triumph the Insult Comic Dog, the White House Correspondents’ Dinner, and Silverman’s show soon followed.
At I Love You, America, Desai joins about 10 writers—including fellow Tiger John Haskell ’07. The show, headed by a mellow-but-still-caustic Silverman, uses humor as “connective tissue” for a divided America. Through sketches, monologues, and interviews, Silverman engages audiences and subjects both liberal and conservative, rural and urban, young and old.
“Sarah’s using the show to pop her own bubble,” says Haskell, a Latin major who graduated from Trinity magna cum laude. “Maybe she’ll visit a family in Louisiana who were Trump supporters, and the show is literally just them picking each other’s brains, and then you realize these are just all people who’ve experienced some form of change in their life.”
I Love You, America has also made strange bedfellows of Trinity’s Haskell and Desai, who’d never met before joining forces in Hollywood. Haskell, much like Desai, left his original career path—teaching—to chase the comedy dream.
“There was just this ‘feeling’ that took over: ‘I am going to try to pursue comedy full time,’” Haskell says of his ascent. “My family raised me to do a ‘practical’ job, so I never really thought that a career like this would be possible.”
Moving to New York, Haskell worked his way through the crowded stand-up scene, performed on the sketch circuit with friend Arthur Meyer as part of the group Two Really Fun Men, and eventually made his way onto the writing staff for The Tonight Show Starring Jimmy Fallon. There, Haskell met fellow comedian Dan Opsal, with whom he’d go on to co-build a small, absurdist YouTube channel, “Real Big Boys.”
Haskell “gravitates towards very silly stuff… Material that gets a very guttural response out of [him] without having to overthink it.” Along this line of thinking, he’s dressed a desperate-for-work Will Ferrell as a new company spokesman for Little Debbie (replete with bright red curls and blue checkered dress); he’s forced Justin Timberlake and Jimmy Fallon to engage in mundane small talk using nothing but hashtags (because we all have that friend who uses hashtags in person); and he’s staged a yodeling match between Fallon and Brad Pitt, both perched on opposing Manhattan high-rises.
“It’s exciting, seeing something you’ve written go from this idea on a desk to having it performed on TV,” Haskell says.
On I Love You, America, you can see Haskell and Desai’s writing goes beyond the desk to merge into Silverman’s larger voice. While Desai helps write many of Sarah’s monologues, Haskell has a hand in many of the show’s separate sketches, though all the writers typically help with every element of the show.
In one bit, a graphic-tee-clad, risen-again Jesus, played by Fred Armisen, stands in line at a bougie sandwich shop in front of Silverman. He and Silverman launch into predictable riffs—Christ solves a flatbread shortage and sip-steals some Coke Zero by converting it from plain water—complemented with more subversive material: Sarah is miffed when Jesus says she’s special but then proceeds to spread the same love to everyone else in line.
While Haskell has his quirks, Desai’s style trends towards “precise execution,” as evident in his writing for the 2017 White House Correspondents’ Dinner that lampooned both the American media as well as the president.
And you might never suspect it after conversing with the soft-spoken Texan, but Desai can land a roast that will have its victim Googling nearby burn centers. In this vein, Desai was a match made in heaven for Conan’s Triumph the Insult Comic Dog character during a stint with Triumph’s Hulu series in 2016. This production, covering watershed moments ranging from the presidential election to the Chicago Cubs’ historic world series championship, won Desai a Writers Guild Award and an Emmy nomination.
“One day, you’re going to share this memory with your grandchildren!” Triumph proclaims to a (presumably) drunk crowd of Cubs fans celebrating on the streets in Chicago. “Or,” Triumph pauses, singling out two gentlemen looking worse-for-wear, “whoever you take to your AA meetings.”
Even though Haskell and Desai have proven comedic track records at this stage in their careers, they’ll both attest that you can’t write unique, fresh material like this by playing it safe. And at Trinity, both learned that constantly opening yourself up to new voices, collaboration, or influences is the best possible risk a comedian can take.
“When I was at Trinity, I had to take a geology course, and an aerobics course—maybe a Japanese literature course, just all these things covering a variety of topics,” Haskell says. “And that’s what I took from the liberal arts aspect: Opening yourself up to so many different points of view is super helpful because it forces you to think outside of just one specific mindset.”
Desai says his college degree actually ended up being a perfect set of credentials for the job he has now—even if it didn’t originally seem that the biochemistry major was making a rational career move back in 2005.
“When I hear people beating up on liberal arts education, or saying people should pursue more practical careers, I totally get it. I’m also a science major, and I think it’s great,” Desai says. “But at the same time, so much of my critical thinking—even if I’m writing a script now, or reading someone’s book, or watching a movie, or watching comedy—that came from the way Trinity approaches the liberal arts.”
More than 1,300 miles away from Hollywood, Samantha Grubbs ’13 has cornered another victim in a San Antonio back alley, hidden under a roaring interstate overpass. But Grubbs isn’t here for a wallet—she’ll settle for some personal trauma.
Grubbs, a communication major and current bank marketing manager from New Iberia, La., is part of Missed Opportunity, an eight-woman improv comedy team founded at Trinity. The group begins every show by asking an audience member to share a personal missed opportunity—a risk they regret never taking. These “bits of trauma” can range from someone not following their boyfriend to Germany, a student going on a lackluster spring break with their family instead of a more unhinged one with friends, or getting married before finishing college.
With this embarrassing anecdote in hand, Missed Opportunity constructs a rapid-fire series of riffs, skits, brand-new characters, and running gags on the spot, all based around that night’s theme. As improv warrants, there’s no set, no props besides the four chairs for the group, and no script—just instinct.
“We’re that group of funny female friends that get together, and we’re giving you a fun, funny, smart show,” Grubbs says.
The group began in January 2016 as a 100-percent Trinity team, performing on campus at the Café Theater. Eventually, they moved to the San Antonio Playhouse, and then to Bexar Stage in 2017. As members move away, the group will occasionally audition some talent from outside the Trinity bubble—including members Tina Jackson, Ariana Cuellar, Morgan Williams, and Alexandra Flores—but the group always maintains a solid maroon core of current students, alumnae, and even faculty.
At a Missed Opportunity show, you’ll probably first take note of Kerry Madden ’20. A communication and theater double major from Austin, Madden loves “moving her hands, making physical choices, and playing the wacky characters.”
“People see a woman in improv, and they assume, ‘Oh, you’re good at playing Mean Girls characters.’” Madden says. “But I’ll jump in as a construction worker who’s really into brick, or a 1920s magician, or a small business-owning ice cream scooper who thinks they’re going to become the mayor of the town.”
As Madden’s characters crash into a scene, you’ll see Liz Metzger ’19 step in to build a world around them. A communication major from Houston, Metzger is “all about creating an environment.” At every performance, Metzger will take a part of her day—things she’s heard in a gender studies class, rants that she’s gone on—and work them into each scene.
And students aren’t the only ones in the spotlight. J’Leen Saeger, a visiting Trinity Spanish professor from Riverside, Calif., brings a frenetic change of pace to the group. “I have been described,” Saeger laughs, “as having the energy of a paint can shaker. I’m very physical, and I bring energy to the table.”
While Grubbs can get wacky herself, she truly shines as a measured, relatable foil to this manic mania. “I’m the straight character a lot—I’m trying to make sense of what everyone else is doing,” Grubbs says. “And you need to be a team player to do that. While other people are playing wacky characters, I’m trying to create a world around them, trying to justify the wacky things they’re doing, to make it more real.”
For all the diverse skills these performers bring to the table, Missed Opportunity still find themselves pushing back against a comedy environment that often offers prejudice instead of respect.
Out on the live circuit, the group sometimes gets half-handed, condescending introductions from male hosts. The group still laughs—and simmers—at one incident where a fellow comic introduced the team by saying, “And now we bring up Missed Opportunity, who’ll show you women can do some things right.”
But for Missed Opportunity, that’s just more fuel for the fire. “I can’t even remember what our ‘missed opportunity’ theme was during the night that happened,” Metzger says. “Instead, we turned that terrible intro the guy gave us into the gag.”
“Moments like that, that’s why I joined Missed Opportunity,” Saeger says. “To see a group of women push back, doing something that’s typically male-dominated—it’s been amazing.”
But the group doesn’t want to define itself as “female-focused” or measure their success by how many punchlines and body blows they land on the patriarchy’s soft underbelly. For Grubbs and Metzger, the draw of Missed Opportunity has always been about a bigger perspective than that. “Yeah, we talk about issues that are important to women, but we’re playing diverse characters,” Grubbs says.
That diversity comes from the groups’ real-world strengths and skills, Metzger adds. “Some of us have doctorates, some are architects, and we’re all in different stages of our lives,” she says. “And you know what? It’s great to bring that to improv because I think that makes our performances more interesting and rich because we come from all these different places in our lives, and that makes the environments we create on stage that much richer.”
“I love being pushed to be better by the people I’m around,” Madden says. “At Trinity, and with Missed Opportunity, you’re able to surround yourself with people who inspire you—people you want to emulate.”
“At Trinity, you learn to work with those people, to create something bigger than yourself,” Metzger says. “You can do that at Trinity because we’re a small school, and there’s just so much support for you. Here, I’ll see J’Leen all the time on her way to class. Sam is in my sorority, and I have an old jersey of hers. Alumni, faculty, and even our librarians will come to our shows. Trinity reinforces these small little connections that go beyond our performances.”
Trinity is known for giving students a “safe space to fail”—a supportive environment to sink your claws into the turf, leaping past the low-hanging fruit and out onto a more precarious tree limb, knowing there’s a soft landing beneath.
But for comedians like Desai, Haskell, Grubbs, Saeger, Metzger, and Madden, the true value of this approach is teaching yourself to keep taking risks. “I would say at age 22, I was just not happy or fulfilled, and there are a lot of people who can say that,” Haskell says. “But if you’re going to try something new, you’ve got to make your move. If it doesn’t work out, you can always reroute and do something else.”
And that philosophy carries over to improv, where each show is a chance to try something new. “With improv, there’s no script, so every move, every decision you’re making is taking a risk,” Saeger says. “I can have the worst day, but when I’m with my girls and we have a great show, it changes the entire course of my weekend: I’m re-energized, and that carries over to other parts of my life.”
Taking risks means surrounding yourself with mentors who ask, “Why not?”
“At Trinity, I had some really terrific professors who were understanding of my general searching and head-up-my-a**-ness” Desai says. “(Retired chemistry professor) Michelle Bushey was my adviser, and she must have written me letters of recommendation for so many different things, but when I talked about comedy, when I talked about creative outlets, she never asked me, ‘Why are you changing your mind?’”
And at Trinity, this type of risk-taking means stepping past your inhibitions, and up to the mic.
Grubbs came to Trinity with a “huge fear of public speaking,” to the point where her hands and voice would shake before every presentation. After taking a risk with improv, she started presenting more and speaking up in class.
“Now, when I perform, it’s just like the audience isn’t there anymore,” Grubbs says. “It’s just me and my girls onstage. And Trinity gave me that opportunity to work on myself, to get myself to that point, and it gave me this group of girls that are smart, funny, and creative. Without that, there’s no show.”