Tim Meadows was once the longest-serving cast member on Saturday Night Live. These days, he’s subtly stealing scenes as the third lead on the CBS sitcom, DMV. But despite plenty of ups and downs over the course of his nearly 40-year career, Meadows seems to be at peace with his particular level of fame.
In this episode of The Last Laugh podcast, Meadows traces the arc of his career, from his unusual path to Lorne Michaels’ office to the disastrous attempt to turn his most popular recurring character into a full-length feature film. He reveals why he really didn’t want the actual Monica Lewinsky to make a cameo as herself with The Ladies Man Leon Phelps—and what changed his mind.
Meadows also explains why he ultimately decided to leave SNL after 10 seasons, the late-night TV gig he now regrets turning down, and how he found creative fulfillment playing supporting roles in films like Mean Girls and Walk Hard.
Meadows was initially hesitant to take on the role of Gregg on DMV because he was described in the pilot script as a former teacher and, as the actor puts it, “I’ve played a lot of teachers in my career.” He started out as the “young, handsome” principal in 2004’s Mean Girls before moving on to play middle-aged teachers in sitcoms like The Goldbergs and Schooled.
After he was cast as a college professor opposite Nicolas Cage in the movie Dream Scenario, he told his agent, “No more teacher parts.” But he made an exception for DMV, in which he plays a grizzled ex-teacher who is forced to take on the even more demeaning job of driving test examiner.
Before he entered the wearing-a-sweater-vest-and-yelling-at-kids phase of his career, Meadows was best known for his impressive 10-season run on SNL, which he joined in 1991 without ever having to go through the traditional audition process, and left in 2000. At that point, no one he had started with on the show was still in the cast.
It wasn’t until Meadows’ seventh season that he debuted what ended up being his first real recurring character, the self-described “Ladies Man” Leon Phelps. He says making that character work on the show “validated that I could do something that was really underground and really edgy and get it on TV.”
“This sounds ridiculous, but I really was not trying to get a recurring character,” Meadows adds. “I was just trying to write funny sketches every week. And if something hit that would be possible to recur, then it would just happen naturally.” Phelps was born out of a “crank phone call voice” that felt embarrassing to do in front of people. “I didn’t want people to know about it,” he says, “so I would’ve never done that as an audition.”
“I thought of it as something that if people found out about, I would get arrested,” he continues. “So it was like a deep, secretive thing that I kept hidden.”
The Ladies Man sketches were far and away the most successful pieces Meadows did on SNL, recurring 26 times between the fall of 1997 and 2000. Perhaps the most memorable installment, in May of 1999, featured a cameo from a 25-year-old Monica Lewinsky, who was just emerging from being a national punchline in the Bill Clinton sex scandal.
“We were told during the writers’ meeting that she was available for sketches that week,” Meadows recalls. “I think Lorne told us to write a Ladies Man, and I was against it, to be honest. I didn’t want to do it.” Meadows says he was never a fan of sketches where the real person comes on and makes fun of themselves on the show—a practice that has only become more common in the years since, with cameos from political figures like Hillary Clinton, Sarah Palin, and Kamala Harris alongside the person impersonating them.
In Meadows’ view, a lot of people had been “hurt” by the Clinton scandal—Lewinsky most of all—and he “just felt like it was just a weird thing for us to be having her on.”
But once he met Lewinsky that week at 30 Rock, he changed his mind. “She was the sweetest person, and I thought about all the stuff that she’d been through,” he says. “So yeah, when I met her, it changed everything. I told her right before the live show, let’s just have fun. I said, if you mess up or you say something off the cards, it’s fine.”
One of his “favorite moments” in that sketch was a joke towards the end where Leon Phelps tees up “the one question that’s on everybody’s mind.” As Lewinsky braces herself, he asks, “Just exactly how big… do you think the opening weekend for Star Wars will be?” Her prediction? “Huge.”
Meadows made sure she was OK with even alluding to that aspect of the scandal and she said, “Yeah, we can do that joke.” It got one of the biggest laughs of the night.
Ultimately, the success of the Ladies Man character on SNL did not translate into box-office gold for the 2000 film version, as had been the case with the Wayne’s World movies a few years earlier. “Not to say that I didn’t want to do a movie, but I knew how popular the character was,” Meadows admits. “And it was not Wayne’s World popular. It wasn’t even A Night at the Roxbury popular. So, I wish it had done better. And yeah, it was disappointing. But the thing I learned from it was to not get caught up in worrying about the success or failure or something. Just because it wasn’t a success didn’t mean that it wasn’t a good movie. The movie is probably 90 percent what we wanted it to be.”
Meadows had hoped that project might be his entrée to movie stardom, as had been the case for some of his former castmates like Mike Myers or Will Ferrell. It’s part of what drove him to leave the show after 10 seasons earlier that same year.
“I remember Lorne telling me at one point that I could work there as long as he worked there,” Meadows says. “He was like, you can stay as long as you want. But I just kind of felt like one, I’ve got to give other people a chance to work here. And the other thing was, I was getting burnt out on trying to come up with something every week. And at the time, people didn’t stay as long as they do now.”
A quarter century ago, Meadows held the record for longest-serving cast member at 10 seasons. Now, Kenan Thompson, who joined SNL in 2003, is currently in his 23rd season.
“Kenan is perfect for that show,” Meadows remarks. “But for me, it was just time to go. I don’t regret it at all. I had some ups and downs after SNL, but you just have to see what’s out there.”
Listen to the episode now and follow The Last Laugh on Apple Podcasts, Spotify, or wherever you get your podcasts to be the first to hear new episodes when they are released every Wednesday.
