Vince Vaughn made his first Hollywood splash playing a cocky retro-hipster in the indie film "Swingers" (1996), which nailed the twenty-something bachelor lifestyle, instantly becoming a cult classic. The 6’5” wiseass subsequently waded through bland dramas and several puzzling misses – Gus Van Sant's “Psycho” (1998), for one – before his fast-talking charm finally found a home in mainstream comedies like “Old School” (2003), “Dodgeball” (2004) and the $200 million box office wonder, “Wedding Crashers” (2005). Vaughn was often referred to as a member of The Frat Pack — a team of actors including Will Ferrell, Ben Stiller, and the Wilson brothers — who generally appeared in the top-grossing comedies of the decade. An unexpected turn in Sean Penn’s “Into the Wild” (2007) suggested that Vaughn might still have a dramatic career ahead of him once he was aged out of the “frat.”

Vaughn was born on March 28, 1970, and raised in the suburbs of Chicago, IL. His father was a sales rep and his mother a successful stockbroker, but prior generations of Vaughns had been, of all things, farmers. The family ethic was very much about Midwestern hard work over upward mobility. Vaughn’s background made him feel out of place in their tony neighborhood, and with average talent in schoolwork and sports, he discovered that his sense of humor was the best way to get positive attention. He began doing local children’s theater from around the age of eight, performing in school plays throughout junior high and high school. He also cultivated his wisecracking, off-the-cuff humor as the host of school variety shows. At some point during his junior year, Vaughn shot up to his adult height of 6’5” and was destined to stand out in a crowd no matter what he did. As president of his senior class at Lake Forest High School, Vaughn’s middling grades almost prevented him from graduating, but he was starting to show definite promise as an actor.

After following a friend to an audition for an industrial film, he ended up coming home with a role himself. Soon after, he enrolled in classes at the famed Improv Olympic and found an agent. He booked a number of commercial jobs, including a high profile Chevy ad, and thus, decided to move to Los Angeles. His highest hopes were that he would be able to make some money doing commercials or getting bit parts on TV shows, never imagining he would become a movie bankable star.

In California, Vaughn began taking acting classes and initially did pretty well with his humble agenda. In 1989, he made his primetime acting debut on "China Beach" (ABC, 1988-1991), and over the next few years he had significant roles in "CBS Schoolbreak Specials" and guest spots on "21 Jump Street" (Fox, 1987-1991) and "Doogie Howser, M.D." (ABC, 1989-1993). When he was not acting, he put his engaging gift of gab to use as a telemarketer.

In 1993, Vaughn landed his first big screen role in the football flick "Rudy,” where he struck up a friendship with co-star Jon Favreau. An up-and-comer himself, Favreau was working on a script about life as a struggling young actor looking for love in the sometimes bitter, ugly Hollywood scene. He wrote a part for Vaughn as his slang-tossing, falsely confident sidekick, so when the indie film was completed several years later, they had unwittingly created a portrait of a time and place that resonated strongly with legions of young, creative city-dwellers. The film was one of the most buzzed-about indies of the year and both actors were catapulted instantly into the spotlight, with Vaughn’s darkly handsome bad boy persona turning him into an overnight "it boy." Such was the closeness of their friendship that the Vaughn hype overshadowing the less showier creator of the film, Favreau, did nothing to impede their bond. In fact, Favreau knew he could never compete with Vaughn’s quicksilver tongue and charm, so was more than happy to be his straight man in future projects and in life itself. In fact, he was such a fan of his wacky friend’s linguistic skills, that he often let Vaughn adlib within scenes he had written or based situations in his scripts on something Vaughn had said or done at one time.

Following the trendy success of “Swingers,” the mildly ambitious Vaughn was stunned to receive an offer from none other than uber-director/producer Steven Spielberg to appear as a lead in the highly anticipated sequel, "The Lost World: Jurassic Park" (1997). The film was a box office smash, and like it or not, Vince Vaughn was on his way to becoming a movie star. Although the film was suitably high profile, it lacked the luster and magic of its predecessor, so was quickly forgotten – as was Vaughn’s middling performance. It was clear even then that his forte was comedy or odd indie flicks – not big budget effects-laden films.

The chatty wit and unflappable confidence that had made Vaughn so appealing in “Swingers” was sadly underused in his next few roles as the actor tried to navigate his way through the web of Hollywood offers, playing the game and taking home the big paychecks. After working with Kate Capshaw in the romantic drama "The Locusts" (1997) he was somewhat subdued as a conflicted, conscience-stricken hedonist in "Return to Paradise" (1998). He thankfully turned on the witty charm to play a gregarious double-crossing trucker in "Clay Pigeons" (1998) before he was woefully miscast to step into Anthony Perkins’ shoes in the Gus Van Sant redo of "Psycho" (1998). The shot-by-shot remake left most critics and audiences asking “why?” Whereas Perkins had projected an androgynous fragility, Vaughn went for sheer madness and the difference was jarring. The actor offered a slightly better turn as a suddenly single father coping with career and familial demands in the little-seen "A Cool, Dry Place" (1999) but again, the role failed to capture the essence of the actor’s appeal. He went on to deliver a stilted performance as an FBI agent who enlists the aid of a psychiatrist (Jennifer Lopez) to track down the victim of a killer in the overproduced "The Cell" (2000). Again – all these projects, no matter the quality – offered no glimpse of what had made Vaughn a star in the first place.

Vaughn’s other projects in 2000 proved a mixed bag, though one had to give the actor credit for making unexpected choices in an effort to discover his niche. His turn as the foster brother on the wrong side of the law in "South of Heaven, West of Hell" (2000) — singer Dwight Yoakam's directorial debut — was hardly memorable. But Vaughn gave a fine turn in the low-budget indie "The Prime Gig" (2000), essaying a slick telemarketer who has the misfortune of working for the wrong businesses. His loose, sexy charm dovetailed with the script and allowed the actor to offer one of his better performances.

Similarly, his long-awaited re-teaming with Favreau in the gangster-themed "Made" (2001), proved to be inspired. The two old friends brilliantly riffed with one another and veered hilariously from the page in the largely improvised film. Vaughn's unwavering characterization of Ricky as a dense but captivating man-child who follows all the wrong instincts proved to be the centerpiece of the film, both when bouncing off the rightfully restrained Favreau or squaring off against veteran scene-stealers like Peter Falk. Fans were ecstatic that at least Favreau could bring back the Vaughn of old.

Unfortunately, the actor’s script-picking instincts took another downward turn for his next film – 2001's lackluster thriller "Domestic Disturbance," in which he played the secretly villainous stepfather to John Travolta's biological son. The film had few admirers, but amid a muddled script, Vaughn turned in a winningly sleazy performance, prompting critic Roger Ebert to note that the actor "plays a creep better than just about anybody else." Some residents of the North Carolina town where the film was shot were inclined to think that Vaughn was an offscreen creep as well, following his assault arrest for a bar fight involving a local resident. Co-star Steve Buscemi reportedly tried to make peace between the parties and ended up with stab wounds and a head full of stitches.

Finally, it appeared that Vaughn was beginning to focus on his underutilized comedic and improvisational skills, perhaps as a result of his memorable role in “Made.” His performance in a short film aired during the 2003 MTV Movie Awards as Hollywood "ass wrangler" Frank Fanning — in which he tutored Drew Barrymore, Lucy Liu and Cameron Diaz on the proper ways to best display their posteriors on camera — was a comedic gold mine. Vaughn likewise surprised audiences with his deft turn guest-hosting CBS's "The Late Show" (CBS, 1993- ) in 2003 when David Letterman fell ill with shingles. And the actor’s career was about to graduate to the next level with the broad comedy "Old School" (2003), where he played one of a trio of disillusioned middle age men who retreat from their boring lives to start a frat house. The following year, with his role as comedic crime kingpin Reese Feldman in the 1970s cop parody "Starsky & Hutch" (2004) with Ben Stiller and Owen Wilson, Vaughn was officially a member of Hollywood’s “Frat Pack.” The actor had at last found a suitable match for his fast-talking, improv-style delivery, and it stood out alongside the era’s blockbuster comedy stars Ben Stiller, Owen Wilson, and Will Ferrell, among others.

In 2004, the newest Frat Packer took the lead in "Dodgeball" (2004), as the charismatic owner of the Average Joe gym who pits a team of misfits against Stiller's brutal pros in a high-tech match. He followed up with a pivotal role as Will Ferrell’s competition in "Anchorman: The Legend of Ron Burgundy" (2004). Then Vaughn turned in one of his most hilarious turns, playing the craven hip-hop talking, pimp-dressing music manager Raji in "Be Cool" (2005), the entertaining sequel to "Get Shorty" in which he improvised much of his non-stop barrage of urban-speak.

After a small, highly amusing role in the Brad Pitt/Angelina Jolie spy-themed action blockbuster "Mr. & Mrs. Smith" (2005), in which he played Pitt's mama's boy partner, Vaughn teamed with Owen Wilson for his biggest hit yet. In the runaway blockbuster "Wedding Crashers" (2005), Vaughn and Wilson co-starred as a pair of lovable cads who pick up lonely, vulnerable women by invading strangers' weddings, only to find themselves entangled with a pair of sisters in a family that threatens to be their undoing. In the fall of 2005, Vaughn revisited his high school variety show roots with the launch of “Vince Vaughn’s Wild West Comedy Show,” a tour featuring improv, sketch comedy, and stand-up from comics Ahmed Ahmed, John Caparulo, Bret Ernst, and Sebastian Maniscalco. The tour, which also featured performances from Vaughn himself, was followed by a camera crew and slated to be released as a documentary in early 2008.

In 2006, Vaughn took on his first producing project with the revenge comedy “The Break-up” (2006), co-starring himself and Jennifer Aniston as a divorcing couple struggling to continue to cohabitate. Critics generally skewered the movie, calling it a watered-down take on “The War of the Roses,” but it was huge at the box office, thanks in part to rumors of a budding relationship between the two stars. It was during the film’s Chicago filming during the summer of 2005, that Aniston was being invaded daily by the paparazzi, in light of her recent split with Brad Pitt and his obvious hook-up with his “Mr. and Mrs. Smith” co-star, Angelina Jolie. In effect, the heartbroken Aniston needed a kind of attention only Vaughn was able to provide and he quickly became quite enamored with and protective of his fragile co-star. Eventually they came clean about their romance, which lasted 18 months. It was also the first time Vaughn’s romantic exploits had been followed nightly by the intrusive press, so an adjustment he was forced to deal with to be with the high profile Aniston. Following their own real-life break-up – with rumors circulating that Aniston may have turned down Vaughn’s marriage proposal – the new bachelor reportedly left the spotlight of Hollywood and bought a home in Chicago.

In 2007, Vaughn appeared in two wildly different films — the gripping adaptation of Jon Krakauer’s “Into the Wild” and the wacky holiday offering “Fred Claus.” In Sean Penn’s chronicle of an idealistic young man’s solo journey into the wild, Vaughn had a small role playing the South Dakota farmer who befriends the drifter after picking him up on the highway. The poignant drama received Oscar buzz from early on, which would mark Vaughn’s first association with work of such caliber. There would likely be no such Oscar talk surrounding his second release of the year, in which he played the troublesome younger brother of Santa Claus (Paul Giamatti) roped into making toys to pay off a bail bond. But regardless of whether his films hit or missed, a limitless supply of goodwill from fans seemed to follow him from project to project – because, simply put – there was no one like him, with his razor-sharp wit and fast-talking persona. Even fellow comics of considerable caliber – from Owen Wilson to Jon Favreau to Will Ferrell – bowed down to his linguistic brilliance.