Tim Meadows has been making an indelible impact on the world of American comedy for the past thirty-five years as an actor, writer, stand-up comic as well as one of the greatest sitcom guest stars in the business. He spent the entire decade of the 1990s as a writer/performer on SNL—which makes him one of the top five longest-serving cast members in that venerable institution’s history—but he’s also built a unique and thriving comedy career on his own terms for the past twenty-five years.
As one of the unquestionable masters of supporting roles and guest appearances in TV comedy, Meadows has scored big with comedy fans. He’s appeared as Jonathan Glascott in nearly fifty episodes of “The Goldbergs” plus two seasons of its spinoff “Schooled” to go with a hilarious turn as an affable cannibal inmate on “Brooklyn Nine-Nine” and an absolutely insane sketch appearance on “I Think You Should Leave.” And let’s not forget his beloved turns as the principal in both the 2004 teen classic “Mean Girls” and its musical reboot in 2024.
He’ll be bringing his magic to the stage of The Den Theatre on May 30-31 for three shows that put him in front of his favorite audiences of all: Chicagoans. Serving up funny stories on divorce, fatherhood, showbiz and much more, the Detroit native took the time to explain the secret behind his success across so many platforms.
“I always try to think of things that will make Chris Farley laugh when I’m working—when I’m doing things I think like, if I did it like this, it would make him laugh,” he says. “Every time I have something that I know is comedic—not like something that’s straight—I think of what would make him laugh if he was playing that part across from me, or if he was watching it on the monitor.
“I’m not really harnessing anything except I’m doing something that I think will make my friend and my other friends laugh, like Adam Sandler or Chris Rock or whoever. And I love all the forms of comedy I do equally.”
Meadows proudly notes that “I became a man in Chicago,” while starring in Second City revues in the second half of the 1980s. He jumped to SNL in 1990 alongside his fellow Second City castmate Farley. His experience writing sketches for Chicago’s most hallowed stage prepared him well for making a big and lasting splash in the late-night favorite.
“I wrote for myself, so I think that helped a lot. That helped too with the longevity, and then once I established myself, kind of like Kenan [Thompson], writers began to write for you, and they knew exactly how to write the things that make them laugh, or things that you do that are funny,” recalls Meadows. “So it became, in my later years on the show, how I scored more—because the writers knew how to write for me, and they wanted to write for me because they knew I could do it.”
His most popular “SNL” character was “The Ladies Man,” a smooth-talking and hilariously risqué guy who offered his tips for sensual success in numerous memorable sketches that eventually made the leap to the big screen with his very own feature film. Meadows credits his formative years in Detroit with creating the inspiration for the unforgettable master of love, Leon Phelps.
“I give credit to Bill Murray and the Carl character from ‘Caddyshack,’ because I kind of use that sort of attitude when I do the character. The character was sort of based on the lifestyle men that I used to see when I was working in Detroit at a liquor store, and they would come in and buy liquor on the weekend, and they always had hot girlfriends. And I was always surprised, because they were, like, just factory workers.
“So when we were writing ‘The Ladies Man,’ I always imagined what kind of love advice those guys would give somebody, and then the rest of it is really created by Harper Steele and Dennis McNicholas, two of the writers that I did it with. That character, when we wrote it, a lot of it was just to make each other laugh. It was like, I bet you won’t get away with saying this, you know. And we would challenge each other, and we’re coming up with the dirtiest or cleanest way to say something dirty.”
Meadows is having a hot year on TV again, with key roles in the popular HBO Max superhero series “Peacemaker” with John Cena, and in a return to network television in the fall CBS sitcom “DMV.” There’s little doubt that those performances will reach yet another generation that will propel his stand-up career forward for at least another decade.
“My fans come out and say ‘he does nothing but score,’ but it’s because my friends know me very well and create the perfect roles for me to jump into,” he concludes. “I’m pretty lucky that people like Adam Sandler or Andy Samberg and the [comedy filmmaking trio] Lonely Island know me very well, and I know how to take things and make them better.
“I’m not a leading actor. I’m the guy who comes in and repairs the plumbing,” he laughs.
Tim Meadows performs at 7:15pm, May 30, and 7:15pm and 9:30pm, May 31 at The Den Theatre, 1331 North Milwaukee. Tickets are $24-$43 plus fees. Visit thedentheatre.com or call (773)697-3830.
