Who Is Rita Wilson: ‘The Masked Singer’ Guest Judge Raps Naughty by Nature

Rita Wilson served as a guest judge on The Masked Singer on Wednesday night, and the contestants weren’t the only ones performing during the show. Following Chameleon’s performance of Warren G and Nate Dogg’s “Regulate,” Wilson pointed out that the masked star wasn’t the only one who could rap.

“You know, you might have a competitor, Chameleon. You may not know this about me, but I can spit some flow,” she said. After fellow judges Robin Thicke and Jenny McCarthy encouraged her to demonstrate, Wilson began to rap Naughty by Nature’s “Hip Hop Hooray.” Though she laughed at the beginning of the impromptu performance, the 64-year-old quickly got into the song and finished with a flourish. “That’s classic television right there,” host Nick Cannon declared as Chameleon gave Wilson two thumbs up.

Wilson is an actress, singer, songwriter and producer who has appeared in a number of films including Volunteers, Sleepless in Seattle, Now and Then, That Thing You Do!, Jingle All the Way, Runaway Bride and Larry Crowne. She has released four albums — AM/FM, Rita Wilson, Bigger Picture, and Halfway to Home — and has produced multiple films including My Big Fat Greek Wedding. In 2019, she received a star on the Hollywood Walk of Fame. She has been married to Tom Hanks since 1988 and the couple shares two sons, Chet Hanks and Truman Hanks. She is also stepmom to Colin and Elizabeth Hanks and has three grandchildren.

Wednesday night was not the first time Wilson has publicly rapped “Hip Hop Hooray” — she covered the song on Instagram in March 2020 while in quarantine after contracting COVID-19 and, following her video’s positive reception, released an official remix of the song with Naughty by Nature one month later to raise money for MusiCares COVID-19 Relief Fund. Wilson shared on Instagram that she actually learned the song for her role in the 2019 film Boy Genius, which took her a month because “Hip Hop Hooray” is “so complex and nuanced; it was like training for a marathon. The rhythms and tempos are so unique and creative.”

The actress explained that while she was in quarantine, she “wanted to see if I still remembered it, kind of like a brain exercise. To my surprise I did.” “I thought it would be fun to put it on my Instagram to show people I was doing okay and to make them smile,” she wrote, thanking Naughty by Nature for teaming up with her. “When @naughtybynature4ever commented about it, I couldn’t believe it. What a joy to be doing this remix with legends of the Hip-Hop world. I’m forever grateful for their generosity of spirit and for being able to raise money together for @musicares COVID-19 Relief Fund.”