2005

Vince Vaughn

September 12

Road Warrior

Vaughn kicks off his Wild West Comedy Show tour in L.A. Serving as the show's emcee, he assembles a group of his unknown comic pals and hits the road for a 30-day, 30-gig schedule that closes in Chicago on Oct. 11. As the host, Vaughn pokes fun of himself onstage, showing an old clip of an ABC afterschool special about sex that featured him.

Vince Vaughn

October 14

Meet the Parents

After spending several days in Chicago openly cuddling and kissing costar Aniston, Vaughn takes his new rumored love to the Lake Forest neighborhood where he grew up. They have lunch with his mother and stepfather. "Vince brings out something in Jennifer that brightens her," a source tells PEOPLE. "She's constantly belly-laughing when they're together. It's a joy to see."

2006

Vince Vaughn

June 02

Premiere Performance

The Break-Up opens and earns more than $39 million in its opening weekend. It's a vindication for Vaughn, who conceived the project in 2003. "I had her in mind when I was writing because I wanted someone who was good with comedy but also a good actor," Vaughn tells EW of Aniston. "There was no second choice."

December 05

The Real Breakup

After months of denying both an engagement and impending breakup, reps for Vaughn and Aniston tell PEOPLE exclusively: "Jennifer and Vince mutually agreed to end their relationship but continue to be good friends today."

2007

Vince Vaughn

March

Ho! Ho! Ho!

After appearing in Sean Penn's Into the Wild, Vaughn cashes in his biggest payday yet – $20 million – when he stars in the holiday comedy Fred Claus. Opposite Paul Giamatti and Rachel Weisz, Vaughn plays Santa's black-sheep brother.

Photo Credits

BIOGRAPHY (top to bottom): WALTER MCBRIDE/RETNA; P/M/BAUER-GRIFFIN; RIQUET/RRG/BAUER-GRIFFIN; Everett

Edited by Mai Dinh, Janet Murphy