A visual history of Tiger Woods' best (and most painfully awkward) celebrity encounters

Pro-Ams, Late Night, Tiger Jam, and one unforgettable TRL appearance. Tiger Woods' run-ins with celebrity over the years have been various and hilarious—a snapshot of a kid growing not only into a legend, but also his own jeans. So this week, in honor of Tiger's inaugural Celebrity Cup triumph at the Genesis Open, where he toppled the competition alongside Kid Rock, Mark Wahlberg, Jerry Rice, Larry Fitzgerald, and Paige Spiranac, we decided to a look back at Big Cat's best (and most awkward) celebrity encounters ever. Let's fire up the time machine, shall we?

Say yes to the vest.

"So what did you think of Tin Cup?"

Bonding over their shared love of a good f-bomb.

Frosted tips and a leather jacket? Who does he think he is? Phil?

Your vertical stripes are a wonderland.

Um, Brick, before I let you go, are you still having your celebrity golf tournament?

Never. Sleeping. Again. #Unchained

P.S. Kudos to Dave for wearing a golf glove during his Tiger Jam set.

Twinning.

"You know who hasn't won 14 majors, Jim?"