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.

2010

Vince Vaughn

January 02

It's a Wedding, Baby!

Vaughn ties the knot with real estate agent Kyla Weber in a private ceremony outside of his Chicago hometown. The following winter, the newlyweds welcome their first child, daughter Locklyn, on Dec. 18. "I feel so grateful. You know, my wife’s so great," the actor gushes. "But I gotta tell you. Just the minute they come out, so beautiful and just so sweet – I was just so glad that everyone was healthy."

2011

Vince Vaughn

January 14

The Dilemma

The new dad stars alongside Jennifer Connelly and Kevin James in The Dilemma, playing a man who finds out his best friend's wife (Winona Ryder) is cheating on him. "The question of the movie is, how do you tell your friend something he doesn't want to hear without hurting him?" he says, adding that director Ron Howard "did a heck of a job" in the comedy that initially drew controversy for its use of a "gay" joke.

2013

Vince Vaughn

August 17

Son-ny Day

Vaughn and wife Kyla welcome their second child, son Vernon Lindsay. Named after Vaughn's father, the baby boy weighs 8 lbs., 4 oz. and measures 21 inches long. "The whole family is so excited to welcome this sweet boy into the world," says a family friend. "I am sure Vince will have Vernon out on the ball field in no time!"

Photo Credits

BIOGRAPHY (top to bottom): WALTER MCBRIDE/RETNA; P/M/BAUER-GRIFFIN; RIQUET/RRG/BAUER-GRIFFIN; Everett; John P Johnson/New Line; INF; Everett Collection; Michael Kovac/Getty

Edited by Julia Wang

Vince Vaughn

Celebrity Central / Top 25 Celebs

 

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