Relive Kenan Thompson's Funniest “Saturday Night Live ”Sketches in Honor of His 20th Anniversary on the Show

The comedian made his debut on the NBC late show on October 4, 2003, and has been making audiences laugh ever since

Kenan Thompson is celebrating 20 years on Saturday Night Live!

The 45-year-old comedian marks his two-decade-long milestone on Wednesday. He made his debut on the NBC late show on October 4, 2003, and has been making audiences laugh ever since.

Last year, Thompson opened up to PEOPLE about what keeps him coming back to the sketch comedy series.

"It's always new every time," he said on the 74th Primetime Emmy Awards red carpet. "It's exciting like that. It's really exciting to find new, funny things, especially when you're further down your tenure."

Thompson pointed to a few of his recent characters, including Kendrick Perkins and LaVar Ball, as sketch ideas that didn't arise until late into his SNL career. "[My] season 19 I'm finding a character to do," he said. "There's always more to do, and if I'm not in anybody's way or nothing, and they keep calling me, like, what am I supposed to do. Tell them no?"

In honor of the milestone, here's a look back at Thompson’s funniest sketches from Saturday Night Live.

Related: Kenan Thompson Shares Cover of ‘Hilarious and Heartwarming’ New Memoir (Exclusive)

Diner Lobster

After a patron (Pete Davidson) shocks a diner by ordering seafood, Thompson — dressed as a lobster — bursts into song to explain why the crustacean never sells. He is joined by the diner staff (guest host John Mulaney, Cecily Strong and Kate McKinnon) in song.

What Up With That?

Thompson can’t be stopped when he takes on the role of musical host Diondre Cole in this sketch, which also stars Samuel L. Jackson, Lindsey Buckingham (Bill Hader) and Jackie Rogers Jr. (Martin Short).

Family Feud: Extended Family

The family feud becomes all too real during this game show. Thompson, playing host Steve Harvey, is forced to be the middle when a man (Tracy Morgan) and his new wife (Strong) face against his ex-wife (Leslie Jones) and kids.

Related: Kenan Thompson Says There's 'Always More' for Him to Do at 'Saturday Night Live'

Eternal Spark of Love: Office Romance

Thompson — dressed in a sparkly blue blazer — narrates a sketch in which Michelle (Jennifer Lopez) flirts with her new coworker (Jason Sudeikis) but things go awry when she reveals that she is obsessed with ventriloquist dummies.

Cinema Classics: Gaslight

In this classic sketch, Thompson, as host Reese De'What, presents the 1944 film Gaslight and explains how it inspired the popular phrase.

Live Report

A reporter's (Thompson) local news report goes off track when he is shocked to learn a beautiful woman (Margot Robbie) is married to an impressive man (Mikey Day).

Black Jeopardy

Darnell Hayesin (Thompson) returns as host of Black Jeopardy and engages with a contestant named Doug (Tom Hanks), who is the opposite side of the political aisle.

Kenan & Kelly

Thompson reimagines his iconic Nickelodeon 90s sitcom Kenan & Kel with the help of Keke Palmer.

Funeral Service

Two friends (Thompson and Scarlett Johansson) share an unusual musical tribute to their late pal, which leaves fellow mourners confused before they embrace it.

Romance Bookstore

Erotic bookstore employees (Aidy Bryant, John Cena and Thompson) act out the fantasies in the novels they're selling.

First Date

A woman (Gal Gadot) goes on a date with a man, who unbeknownst to her is O.J. Simpson. Over the course of the date, she slowly realizes he is the former running back who made headlines when he was accused of murdering two people.

Related: Kenan Thompson on His Career-Launching Secret Weapon as a Comic: 'I Have a Cute Face'

Prince Auditions

Rami Malek and Thompson face off at an audition to score the role of Prince. Each performer show off his best impression of the “Purple Rain” singer.

Sump'n Claus

Sump'n Claus (Thompson) makes sure there is something for everyone, no matter if you’ve been naughty or nice.

Two Worlds Collide ft. Reba McEntire

Thompson steps into the role of Reba McEntire for a duet with Andy Samberg. While the two share their love for one another, Samberg’s friends question who McEntire really is.

Holiday Gig

A band’s holiday musical performance goes awry when Thompson and Eddie Murphy scrabble on stage.

Come Back, Barack

Thompson, Chris Redd, and Chance the Rapper are longing for the return of  Barack Obama in this throwback R&B ballad. The 2017 song also includes the line, "I'd vote for Joe Biden" long before he became president in 2021.

Related: Kenan Thompson Names the 'SNL' Alum He Wishes He'd Gotten to Work with: 'A Very Close Big Brother'

Strollin'

A group of voters (Thompson, Reed, Ego Nwodim, Punkie Johnson) try to make their way to the polls but they face hurdles including poll worker (Mulaney) turning them away in this sketch, which highlights voter suppression.

Politics Nation: Voter ID Disaster

Al Sharpton (Thompson) and statistical analyst Charles Richards (Al Sharpton) discuss the popularity of various presidential candidates among Black voters.

Them Trumps: State of the Union

What happens if the Trumps (Thompson, Redd and Ego Nwodim) were a black family? This sketch answers that question.

Weekend Update: The Village People on Donald Trump Using Their Music

The Village People (Thompson, Redd, Mikey Day, Beck Bennett, Bowen Yang) make a statement on Weekend Update about Donald Trump using their music at his political rallies.

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