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.

2008

Vince Vaughn

November 26

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

Vince Vaughn

March

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

Edited by Janet Mock