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In 2020, he became the spokesman for Universal Parks & Resorts’ "Let Yourself Woah" campaign, and was set to host the 2020 White House Correspondents' Dinner.

In 2019, Thompson served as a judge for NBC's comedy competition series Bring the Funny. He also became an executive producer with Mitchell for Nickelodeon's All That revival, premiering in June. In May 2019 NBC announced they had picked up Thompson's single-camera comedy The Kenan Show to series. The series will premiere in 2020 and feature Thompson as a newly widowed father determined to be a "super dad."

In 2015, Fandango announced that Thompson would play their brand character, fictional character Miles Mouvay. Thompson would play Mouvay in 18 videos, eight 30-second commercials, and a few comedic skits.

On September 23, 2015, Thompson appeared on The Tonight Show Starring Jimmy Fallon alongside former All That co-star Kel Mitchell in which they reprised their popular Good Burger roles as "Ed" and "Lester Oakes, Construction Worker". They later competed against one another in an episode of the revived Nickelodeon game show Double Dare that aired in November 2018.

In 2014 head writer for SNL, Brian H Tucker noted that simply putting "KENAN REACTS" would get a script more laughs, further elaborating "Put him in your sketch somewhere, anywhere, and your sketch will get better. Because Kenan knows how to take ordinary lines and make them funny, and take funny lines and make them special." Similarly, Lorne Michaels in a 2019 article would refer to Thompson as "the person I most rely on in the cast." Vulture referred to him as the "heir apparent" to Phil Hartman, both being "The glue" of their respective casts.

In 2013, he refused to play any more black women on the show and demanded SNL hire black women instead.

Thompson has been a cast member on SNL for 17 seasons, breaking the record for the longest-tenured cast member in the show's history previously held by Darrell Hammond, who was on the show for 14 seasons. Thompson became the most senior cast member in the second half of the 2013–14 season, following the departure of Seth Meyers. He is also the longest-serving African-American cast member, surpassing Tim Meadows, who stayed on the show for ten seasons, and is also the oldest current cast member. Thompson also holds the record for most celebrity impressions performed on the show, performing 139, beating Hammond's previous record of 107. Although early on he planned to stay on the show until something else came along, by 2019 he noted that SNL was his "Forever plan."

Thompson married model Christina Evangeline on November 11, 2011. Together, they have two daughters, born in June 2014, and August 2, 2018.

In 2009, Thompson was a regular voice actor in the Fox cartoon series Sit Down, Shut Up, portraying Sue Sezno, who, as evinced by her last name, always says no. The series premiered on April 19, 2009, but was canceled after only four episodes due to low ratings and less than favorable reviews. Thompson provided the voice for the LeBron James puppet in Nike's MVP "Most Valuable Puppets" commercials, which were produced to be shown throughout the 2009 NBA Playoffs. Thompson also guest starred on the USA Network series Psych in the fourth season episode "High Top Fade Out". He played an estranged college singing buddy of the character Gus. In 2011, he returned to Nickelodeon, as he guest starred in "iParty With Victorious", a crossover episode of TV sitcoms iCarly and Victorious.

Thompson returned to sketch comedy when he joined the cast of Saturday Night Live in 2003,. According to Thompson he had previously sent an audition tape to SNL multiple times with them claiming he looked too young, with him noting "it was a couple years’ worth of that" A fan of the show before joining, Thompson noted that he feared that being on the show was a "disservice" to it stating "It was weird for me for a long time" Thompson was a featured player until 2005 (spanning the 29th and 30th seasons) and was promoted to repertory player at the beginning of season 31 (the 2005–2006 season).

Thompson began his acting career in the early 1990s, and earned fame as an original cast member of Nickelodeon's sketch comedy series All That. In this time, he often collaborated with All That costar Kel Mitchell. In 1996, they began starring in their own sitcom Kenan & Kel (1996–2000). Thompson is also known for his roles in The Mighty Ducks franchise, Good Burger, and the title character in the 2004 film Fat Albert.

Thompson appeared as a host of sorts of TeenNick's 1990s programming block, The '90s Are All That, appearing in many of the block's early bumpers and hyping material. He would return to the block, now called NickRewind but at the time called The Splat, for All That' s 22nd anniversary, with segments filmed at the 2015 New York Comic-Con.

Kenan Thompson (/ˈ k iː n ə n / ; born May 10, 1978) is an American actor and comedian. He has been a cast member of the NBC sketch comedy series Saturday Night Live since 2003, making him the longest-tenured cast member in the show's history.