- 2005


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.


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


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."
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


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.
- 2008


Another Christmas Flick
With Reese Witherspoon, Vaughn stars in Four Christmases, about a couple that embarks on visiting all four of their divorced parents on Christmas Day. The film opens at No. 1, raking in $31.7 million in its first weekend at the box office.
- 2009


Putting A Ring On It
Vaughn and girlfriend Kyle Weber, a Calgary real estate agent, get engaged. After splitting with high-profile love Aniston in 2006, the funnyman keeps his relationship with Weber ultra-private, revealing only that the foundation of a good relationship is "that you can laugh with each other, that you have fun with each other" in early 2008.
Photo Credits
BIOGRAPHY (top to bottom): WALTER MCBRIDE/RETNA; P/M/BAUER-GRIFFIN; RIQUET/RRG/BAUER-GRIFFIN; Everett; John P Johnson/New Line; INF
- Name
- Vince Vaughn
- Date of Birth
- March 28, 1970
- Birth Place
- Buffalo Grove, Ill.
- Relationships
-
Kyla Weber, fiancée (2008 to present)
Jennifer Aniston, ex-girlfriend (2005 to 2006)
Joey Lauren Adams, ex-girlfriend (1998)




