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Saturday Night Live

Who: Kenan Thompson
Cast Member Since: 2003

Kenan Thompson changed how I think about Saturday Night Live.

Sometime in the mid-1990s, I decided five seasons should be the maximum for any cast member. I initially based this off the original 1975-1980 Lorne Michaels run after which the entire cast departed, but I also noticed a pattern taking shape as I first started watching the show in 1989. Many of the strongest cast members during that time – Jon Lovitz, Nora Dunn, Jan Hooks, Victoria Jackson, Dennis Miller (and eventually Adam Sandler and Chris Farley, who were involuntarily let go) – were gone after five to six seasons. And think of what that group of talent accomplished in just five years. The Sweeney Sisters, Tommy Flanagan, Matt Foley, Pepper Boy, etc. are all Saturday Night Live classics from people who, in retrospect, came and went fairly quickly.

Of course, there were exceptions. Dana Carvey, Phil Hartman, Kevin Nealon, and Mike Myers each stayed between seven and nine seasons, but their output certainly diminished somewhere after that 5-year mark. For example, remember how out of place Myers looked mixed in with the new blood in 1993’s Donkey Basketball? I also thought people like Tim Meadows and Darrell Hammond who hung around for 10+ years stayed well past what was necessary.

Enter 25-year-old Athens native Kenan Thompson in 2003. Like many SNL fans at the time, I was skeptical as soon as the news broke that Summer. I remember wondering why Lorne Michaels would break his pattern of hiring rising stand up and improv comedians to go with a well-known children/young adult series actor best known for All That, Good Burger and Kenan & Kel. Surely Thompson (and 2003’s other new hire, Finesse Mitchell) couldn’t be a one-to-one trade for the recently departed Chris Kattan and Tracy Morgan. In other words, Thompson —the first cast member born after the show’s 1975 premiere— had much to prove.

Revisiting Thompson’s early seasons in 2019 is interesting. He was always confident and competent, but the range we see today was nowhere on the screen. Much of his initial work was made up of Bill Cosby or Al Sharpton impressions as well as simple one dimensional (but funny) characters like DJ Dynasty Handbag, K-Smooth, Virginica Hastings and Jean K. Jean. Considering he was battling for air time along side SNL giants-in-the making like Amy Poehler, Jimmy Fallon, Tina Fey and Seth Meyers, not to mention the other relatively new faces (Fred Armisen, Bill Hader, Andy Samberg, Kristen Wiig), it would be hard for anybody to make a mark in that field.

Jump ahead to Thompson’s fourth and fifth seasons. His time up to that point was entertaining, but far from ground breaking, and with my 5-year rule in place, I was ready to see him exit. Then came What Up With That? in September 2009. This nearly seven-minute segment changed everything I thought about Thompson and, over time, forced me to abandon the 5-year rule. Never before did he appear to be having so much fun on screen. Never before was his humor so absurd. I loved it, and over the course of the next few seasons, Thompson slow began dropping the characters he debuted between 2003-2009 and seemingly focused on being new and silly. It worked. Thompson refined and perfected his Lorenzo McIntosh character, added David “Beef Jelly” Winfield to the Kings of Catchphrase Comedy, introduced us to Reese De’What, Trey from The Californians and Treece Henderson, oh, and don’t forget Reba’s team up with The Lonely Island.

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So what caused the shift? For one, he outlasted the talent he started with and became more confident in the veteran role which likely gave him a larger sense of freedom. He also felt comfortable forcing the show to do certain things his way, like when he famously refused to continue playing African-American women in drag. Staying in one place for 16 years will give you that sort of pull.

Sadly, I’m fairly sure the 2019-2020 season of SNL will be his last. Thompson will be 41 when the season starts, and he’ll also be splitting time with the upcoming The Kenan Show sitcom, also on NBC, where he’ll play the lead. When he does exit, he’ll hold a record for the most celebrity impressions on the show (nearly 130), and hopefully everyone left will pick up his most important lesson: when it is time to retire a character, do it. Can you imagine if we were hearing DJ Dynasty Handbag say “OOOHHH WEEEE Tiara” every other weekend for the last 16 years?

Take a look below at two of Thompson’s best moments from Season 44:

Sketch: Maurice
Episode: Halsey (2/9/19)
NOTE: New character alert: a freelance postal worker how “presents” himself online. Next stop Ellen!

Sketch: Jail Cellmate
Episode: Seth Meyers/Paul Simon (10/13/18)
NOTE: After several years off, Thompson brought back the Bill Cosby impression that worked so well in his first season in 2003. Welcome back!