The Loop

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

February 14, 2019
Tiger Jam 2011

Ethan Miller

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?

Jay Leno - 1996

The Tonight Show with Jay Leno - Season 5

NBC

Say yes to the vest.

Twister-era Bill Paxton - 1997

The Tonight Show with Jay Leno - Season 6

NBC

Kevin Costner -1997

AT&T National Pro-Am

Andy Lyons

"So what did you think of Tin Cup?"

The Dream Team -1998

The Tonight Show with Jay Leno

NBC

Kid Rock and Pamela Anderson - 2001

Tiger Jam IV

L. Cohen

Samuel L. Jackson - 2001

The Ninth Annual ESPY Awards

Kevin Winter

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

Carson Daly - 2002

Tiger Woods Promotes "EA Sports Tiger Woods PGA Tour 2002" Video Game on MTV's "TRL" - March 4, 2002

KMazur

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

Train - 2002

Tiger Jam V At Mandalay Bay Events Center In Las Vegas

Ethan Miller

Stevie Wonder - 2005

Tiger Jam VIII - Show

L. Cohen

Terri Hatcher and Sam Jackson - 2006

Tiger Jam IX Benefit Concert - Backstage and Show

L. Cohen

Sting - 2006

Tiger Jam IX Benefit Concert - Arrivals

L. Cohen

Terri Hatcher and John Mayer -2007

Tiger Woods Learning Center Block Party

Lester Cohen

Your vertical stripes are a wonderland.

Mike - 2007

PGA TOUR - 2007 Wachovia Championship - Pro-Am

Sam Greenwood

Will Ferrell - 2007

Tiger Wood's 10th Annual "Tiger Jam"

Lester Cohen

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

Daughtry - 2007

Tiger Wood's 10th Annual "Tiger Jam"

Lester Cohen

Justin Timberlake - 2008

2008 ESPY Awards - Show

Kevin Winter

Never. Sleeping. Again. #Unchained

Eddie Van Halen - 2008

11th Annual Tiger Jam to Benefit the Tiger Woods Foundation - Arrivals

Lester Cohen

David Lee Roth- 2008

USA - Tiger Jam XI Benefit Concert in Las Vegas

Chris Farina

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

11th Annual Tiger Jam to Benefit the Tiger Woods Foundation - Show and Backstage

Lester Cohen

P. Diddy - 2009

Tiger Jam 2009 With No Doubt

Lester Cohen

No Doubt - 2009

Tiger Jam 2009 With No Doubt

Lester Cohen

Ben Roethlisberger - 2009

Tiger Jam 2009 With No Doubt

Lester Cohen

Tony Romo - 2012

AT&T Pebble Beach National Pro-Am - Final Round

Jeff Gross

AT&T Pebble Beach National Pro-Am - Round Two

Ezra Shaw

AT&T Pebble Beach National Pro-Am - Round One

Jeff Gross

Twinning.

Jon Bon and some guy from American Idol

2012 Tiger Jam

Ethan Miller

Jimmy Fallon - 2014

The Tonight Show Starring Jimmy Fallon - Season 1

NBC

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

Airpods Wahlberg - 2019

Genesis Open - Preview Day 3

Stan Badz