Lance Armstrong & Oprah Winfrey
Prior to the disgraced cyclist's alleged doping admission, Lance was a pretty popular guy. His charity, Livestrong—from which he recently stepped down as chairman—saw support from celebs like Robin Williams, Norah Jones and Matthew McConaughey, not to mention he's dated a slew of Hollywood's hottest starlets. So, let's take a look back at the athlete in his glory days hanging with his celebrity pals, ahead of his rumored performance enhancing drug confession.
Jake Gyllenhaal
The biking BFFs went on a two-hour ride together along the Malibu coast back in 2006.
Ashley Olsen
The unlikely twosome reportedly dated briefly back in 2007.
Matthew McConaughey & Jake Gyllenhaal
The good-looking guys—who were all single when this pic was snapped back in 2006—were often spotted cycling and spending quality time together.
Sandra Bullock & Robin Williams
The Good Will Hunting actor, the Crash star and the cyclist were all smiles at a Men's Journal party circa October 2008.
Eva Longoria
The famous friends posed together at the Beverly Hilton Hotel back in 2006 at a Larry King Cardiac Foundation Fundraising Gala.
Sheryl Crow
The former couple—who spent three years together—called off their engagement in 2006.
David Arquette
The party pals shared a fun night out together in April 2007 at the Safe Harbor Loft in NYC.
Tory Burch
The famed fashionista and the professional cyclist split in 2007 after a brief romance.
Matthew McConaughey
The athletic BFFs were regularly snapped working out—and hanging out—together years ago when the handsome hunks were both single.

