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Come Fan with UsThursday, June 25, 2026

Conan O’Brien loses at ‘Tony Hawk’s Pro Skater 5,’ gets a tattoo of Lil Wayne as punishment

“My board caught on fire! YEAH!”

To celebrate the upcoming release of Tony Hawk’s Pro Skater 5, Conan O’Brien invited skateboarding legend Tony Hawk and Lil Wayne on his show to play the game. Much like the last time he played a video game with an athlete, things got awkward between everyone in the room; it wouldn’t be a Conan O’Brien show without some semblance of awkwardness.
At some point, Lil Wayne trapped Conan in a “that’s what she said” joke loop, which, to be fair, was Conan’s fault for setting him up.

For the main event, Conan bet Lil Wayne in a one-on-one battle in the game -- whoever lost had to get a tattoo of the winner’s head on their body. Of course, Conan lost ... and he delivered:

OK, that’s a drawn-on tattoo of Lil Wayne. But at least it says “I (Heart) Weezy” on it!

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