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?

Jay Leno - 1996

THE TONIGHT SHOW WITH JAY LENO -- Episode 951 -- Pictured: (l-r) Professional golfer Tiger Woods during an interview with host Jay Leno on June 25, 1996 -- (Photo by: Margaret C. Norton/NBC/NBCU Photo Bank via Getty Images)

The Tonight Show with Jay Leno - Season 5

THE TONIGHT SHOW WITH JAY LENO -- Episode 951 -- Pictured: (l-r) Professional golfer Tiger Woods during an interview with host Jay Leno on June 25, 1996 -- (Photo by: Margaret C. Norton/NBC/NBCU Photo Bank via Getty Images)
NBC

Say yes to the vest.

Twister-era Bill Paxton - 1997

THE TONIGHT SHOW WITH JAY LENO -- Episode 1289 -- Pictured: (l-r) Actor Bill Paxton and professional golfer Tiger Woods on December 22, 1997 -- (Photo by: Margaret Norton/NBC/NBCU Photo Bank via Getty Images)

The Tonight Show with Jay Leno - Season 6

THE TONIGHT SHOW WITH JAY LENO -- Episode 1289 -- Pictured: (l-r) Actor Bill Paxton and professional golfer Tiger Woods on December 22, 1997 -- (Photo by: Margaret Norton/NBC/NBCU Photo Bank via Getty Images)
NBC

Kevin Costner -1997

31 Jan 1997: Tiger Woods and actor Kevin Costner confer during the AT&T National Pro-Am at the Poppy Hills Golf Course in Pebble Beach, California.

AT&T National Pro-Am

31 Jan 1997: Tiger Woods and actor Kevin Costner confer during the AT&T National Pro-Am at the Poppy Hills Golf Course in Pebble Beach, California.
Andy Lyons

"So what did you think of Tin Cup?"

The Dream Team -1998

THE TONIGHT SHOW WITH JAY LENO -- Episode 1360 -- Air Date 04/17/1998 -- Pictured: (l-r) Actress Jennifer Aniston, professional golfer Tiger Woods, host Jay Leno, actor Josh Brolin onstage April 17, 1998  (Photo by Margaret C. Norton/NBC/NBCU Photo Bank via Getty Images)

Kid Rock and Pamela Anderson - 2001

Kid Rock, Pamela Anderson, Tiger Woods (Photo by L. Cohen/WireImage)

Tiger Jam IV

Kid Rock, Pamela Anderson, Tiger Woods (Photo by L. Cohen/WireImage)
L. Cohen

Samuel L. Jackson - 2001

Samual L. Jackson and Tiger Woods at The Ninth Annual ESPY Awards at the MGM Grand Hotel in Las Vegas, NV.,  Monday, Feb.12, 2001.   (photo by Kevin Winter/Getty Images).

The Ninth Annual ESPY Awards

Samual L. Jackson and Tiger Woods at The Ninth Annual ESPY Awards at the MGM Grand Hotel in Las Vegas, NV., Monday, Feb.12, 2001. (photo by Kevin Winter/Getty Images).
Kevin Winter

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

Carson Daly - 2002

Carson Daly and Tiger Woods (Photo by Kevin Mazur/WireImage)

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

Carson Daly and Tiger Woods (Photo by Kevin Mazur/WireImage)
KMazur

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

Train - 2002

Golfer Tiger Woods (3rd R) and rock band Train (L-R) singer Pat Monahan, guitarist Rob Hotchkiss, drummer Scott Underwood, Woods, bassist Charlie Colin, and guitarist Jimmy Stafford appear after a news conference at the Tiger Jam V benefit at the Mandalay Bay Events Center April 20, 2002 in Las Vegas, Nevada. The event, put on by golfer Tiger Woods, is held to raise and distribute funds for the Tiger Woods Foundation and children's charities based in Las Vegas and Los Angeles.  (Photo by Ethan Miller/Getty Images)

Stevie Wonder - 2005

Tiger Woods and Stevie Wonder during Tiger Jam VIII - Show at Mandalay Bay Events Center in Las Vegas, Nevada, United States. (Photo by L. Cohen/WireImage for Tiger Woods Foundation)

Tiger Jam VIII - Show

Tiger Woods and Stevie Wonder during Tiger Jam VIII - Show at Mandalay Bay Events Center in Las Vegas, Nevada, United States. (Photo by L. Cohen/WireImage for Tiger Woods Foundation)
L. Cohen

Terri Hatcher and Sam Jackson - 2006

Tiger Woods, Teri Hatcher and Samuel L. Jackson during Tiger Jam IX Benefit Concert - Backstage and Show at Mandalay Bay Event Center in Las Vegas, Nevada, United States. Exclusive (Photo by L. Cohen/WireImage)

Sting - 2006

Tiger Woods and Sting during Tiger Jam IX Benefit Concert - Arrivals at House of Blues in Las Vegas, Nevada, United States. (Photo by L. Cohen/WireImage)

Tiger Jam IX Benefit Concert - Arrivals

Tiger Woods and Sting during Tiger Jam IX Benefit Concert - Arrivals at House of Blues in Las Vegas, Nevada, United States. (Photo by L. Cohen/WireImage)
L. Cohen

Terri Hatcher and John Mayer -2007

(EXCLUSIVE, Premium Rates Apply) ANAHEIM, CA - OCTOBER 06:  Backstage at theTiger Woods Leaning Center Block Party  Singer John Mayer, Actress Teri Hatcher and Golfer Tiger Woods  (Photo by Lester Cohen/WireImage)

Tiger Woods Learning Center Block Party

(EXCLUSIVE, Premium Rates Apply) ANAHEIM, CA - OCTOBER 06: Backstage at theTiger Woods Leaning Center Block Party Singer John Mayer, Actress Teri Hatcher and Golfer Tiger Woods (Photo by Lester Cohen/WireImage)
Lester Cohen

Your vertical stripes are a wonderland.

Mike - 2007

Michael Jordan and Tiger Woods during the Pro-Am prior to the 2007 Wachovia Championship held at Quail Hollow Country Club in Charlotte, North Carolina on May 2, 2007. (Photo by Sam Greenwood/PGA)

PGA TOUR - 2007 Wachovia Championship - Pro-Am

Michael Jordan and Tiger Woods during the Pro-Am prior to the 2007 Wachovia Championship held at Quail Hollow Country Club in Charlotte, North Carolina on May 2, 2007. (Photo by Sam Greenwood/PGA)
Sam Greenwood

Will Ferrell - 2007

Tiger Woods and Will Ferrell during Tiger Wood's 10th Annual "Tiger Jam" at Mandalay Bay Resort & Casino in Las Vegas, Nevada, United States. Exclusive (Photo by Lester Cohen/WireImage)

Tiger Wood's 10th Annual "Tiger Jam"

Tiger Woods and Will Ferrell during Tiger Wood's 10th Annual "Tiger Jam" at Mandalay Bay Resort & Casino in Las Vegas, Nevada, United States. Exclusive (Photo by Lester Cohen/WireImage)
Lester Cohen

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

Daughtry - 2007

(EXCLUSIVE, Premium Rates Apply) Tiger Woods (C) and Daughtry (Photo by Lester Cohen/WireImage)

Tiger Wood's 10th Annual "Tiger Jam"

(EXCLUSIVE, Premium Rates Apply) Tiger Woods (C) and Daughtry (Photo by Lester Cohen/WireImage)
Lester Cohen

Justin Timberlake - 2008

LOS ANGELES, CA - JULY 16:  Host Justin Timberlake peforms as he stands behind a Tiger Woods cutout onstage at the 2008 ESPY Awards held at NOKIA Theatre L.A. LIVE on July 16, 2008 in Los Angeles, California.  The 2008 ESPYs will air on Sunday, July 20 at 9PM ET on ESPN.  (Photo by Kevin Winter/Getty Images)

Never. Sleeping. Again. #Unchained

Eddie Van Halen - 2008

LAS VEGAS - APRIL 19:  Eddie Van Halen and Tiger Woods arrive at the 11th Annual Tiger Jam at Mandalay Bay Resort & Casino on April 19, 2008 in Las Vegas, Nevada.  (Photo by Lester Cohen/WireImage)

David Lee Roth- 2008

(L-R) Tiger Woods and David Lee Roth arrive at the 11th Annual Tiger Jam benefit concert hosted by Tiger Woods and featuring Van Halen at the Mandalay Bay Events Center in Las Vegas. (Photo by Chris Farina/Corbis via Getty Images)

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

LAS VEGAS - APRIL 19:   David Lee Roth of Van Halen performs during the 11th Annual Tiger Jam at Mandalay Bay Resort

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

LAS VEGAS - APRIL 19: David Lee Roth of Van Halen performs during the 11th Annual Tiger Jam at Mandalay Bay Resort
Lester Cohen

P. Diddy - 2009

(EXCLUSIVE, Premium Rates Apply) LAS VEGAS - MAY 16:  Sean "Diddy" Combs and Golfer Tiger Woods attend Tiger Jam 2009 at the Mandalay Bay Events Center on May 16, 2009 in Las Vegas, Nevada. EXCLUSIVE  (Photo by Lester Cohen/WireImage)

No Doubt - 2009

Tom Dumont, Tony Kanal, Gwen Stefani and Adrian Young of No Doubt pose with Tiger Woods (second from R) at Tiger Jam 2009 held at the Mandalay Bay Events Center on May 16, 2009 in Las Vegas, Nevada. EXCLUSIVE Exclusive (Photo by Lester Cohen/WireImage)

Ben Roethlisberger - 2009

(EXCLUSIVE, Premium Rates Apply) LAS VEGAS - MAY 16:  Golfer Tiger Woods and NFL player Ben Roethlisberger attend Tiger Jam 2009 at the Mandalay Bay Events Center on May 16, 2009 in Las Vegas, Nevada. EXCLUSIVE  (Photo by Lester Cohen/WireImage)

Tony Romo - 2012

PEBBLE BEACH, CA - FEBRUARY 12:  Tiger Woods (R) and Tony Romo (L), NFL football quarterback for the Dallas Cowboys, wait on the second tee box during the final round of the AT&T Pebble Beach National Pro-Am at Pebble Beach Golf Links on February 12, 2012 in Pebble Beach, California.  (Photo by Jeff Gross/Getty Images)
PEBBLE BEACH, CA - FEBRUARY 10:  (L-R) Tiger Woods and NFL football quarterback for the Dallas Cowboys, Tony Romo wait on the sixth tee during the second round of the AT&T Pebble Beach National Pro-Am at the Monterey Peninsula Country Club (Shore Course) on February 10, 2012 in Pebble Beach, California.  (Photo by Ezra Shaw/Getty Images)
PEBBLE BEACH, CA - FEBRUARY 09: (L-R) Tiger Woods looks on as football player, amateur Tony Romo, lines up his putt on the 11th green during the first round of the AT&T Pebble Beach National Pro-Am at the Spyglass Hill Golf Course on February 9, 2012 in Pebble Beach, California.  (Photo by Jeff Gross/Getty Images)

Twinning.

Jon Bon and some guy from American Idol

LAS VEGAS, NV - APRIL 28:  (L-R) Recording artist Jon Bon Jovi, golfer Tiger Woods and recording artist David Cook appear at Tiger Jam 2012 at the Mandalay Bay Events Center April 28, 2012 in Las Vegas, Nevada.  (Photo by Ethan Miller/Getty Images)

2012 Tiger Jam

LAS VEGAS, NV - APRIL 28: (L-R) Recording artist Jon Bon Jovi, golfer Tiger Woods and recording artist David Cook appear at Tiger Jam 2012 at the Mandalay Bay Events Center April 28, 2012 in Las Vegas, Nevada. (Photo by Ethan Miller/Getty Images)
Ethan Miller

Jimmy Fallon - 2014

THE TONIGHT SHOW STARRING JIMMY FALLON -- Episode 0110 -- Pictured: (l-r) Golfer Rory McIlroy, host Jimmy Fallon and golfer Tiger Woods during the "Facebreakers" skit on August 18, 2014 -- (Photo by: Douglas Gorenstein/NBC/NBCU Photo Bank via Getty Images)

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

Airpods Wahlberg - 2019

PACIFIC PALISADES, CA - FEBRUARY 14: Tiger Woods and actor/singer Mark Wahlberg watch play on the ninth hole during the Pro-Am round for the Genesis Open at Riviera Country Club on February 14, 2018 in Pacific Palisades, California. (Photo by Stan Badz/PGA TOUR)