Chris Pine Makes Jimmy Kimmel Extremely Uncomfortable As He Raps Vanilla Ice’s ‘Ice Ice Baby’

Cue the cringes! Chris Pine just embarrassed the heck out of Jimmy Kimmel with his hilarious rendition of a classic rap song.

The Wonder Woman actor, 38, gave the talk show host, 51, more than he bargained for while appearing on Jimmy Kimmel Live! on Thursday, January 24, when he launched into Vanilla Ice’s “Ice Ice Baby.”

After sharing that he had been in a band with his math and English teachers in middle school, performing hits such as “Brown Sugar” by The Rolling Stones and “Let’s Get It On” by Marvin Gaye, Pine revealed that the first song he fully learned was none other than the repurposed Queen and David Bowie tune.

When the I Am the Night star praised Vanilla Ice (real name Robert Matthew Van Winkle), 51, for his “fantastic lyrics” on the track, Kimmel challenged him to take the audience through them.

Jimmy Kimmel's Embarrassed Over Chris Pine Rap
Chris Pine with Jimmy Kimmel ABC

The Wet Hot American Summer: First Day of Camp alum didn’t disappoint, using a pen as a microphone to channel the ‘90s rapper. “All right, stop / Collaborate and listen / Ice is back with my brand new invention,” he began.

Pine missed a few words in the second verse, however, making for an adorably awkward moment that had the two men giggling uncontrollably.

“That was a mistake,” the Man Show alum quipped of the performance once he was able to speak. “You shouldn’t have done that.”

“I’m gonna leave now,” Pine joked back. “How am I gonna f—king leave now?”

“That’s it!” Kimmel teased. “You’re out of the next Wonder Woman!”

Viewers had their say in the comments section of the YouTube clip as well: “Cringe,” one commenter wrote, as another chimed in, “Um, Chris should stick to acting.”

It wasn’t his first rodeo, however: Pine previously serenaded a fan, known as a “Pine Nut,” with Frank Sinatra’s “Summer Wind” during an appearance on The Ellen DeGeneres Show in November 2014.

Jimmy Kimmel Live! airs on ABC weeknights at 11:35 p.m. ET.

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