Livingston was born on June 5, 1968 in Cedar Rapids, IA. He and his three siblings were raised in the town of Marion by a Lutheran minister mother and an aerospace engineer father who once considered a singing career. Their sons interest in acting emerged as early as the second grade, with Livingstons portrayal of Rip Van Winkle in a school play. As a student at Marion High School, Livingstons main activities were wrestling on the schools team and acting. His father even joined him in a stage production of Oklahoma. At age 16, Livingston broke the news of his career plans to his parents and upon graduation, trekked to Connecticut to study acting at Yale Universitys prestigious drama department.

At Yale, Livingstons classmates included future stars Edward Norton and Paul Giamatti. At one point, Livingston directed Norton in a production of Chekovs The Cherry Orchard. After graduating from college with degrees in theater and literature, Livingston moved to Chicago, where he first performed in small-staged production of Shakespeare before understudying in various productions at Chicagos Goodman and Touchstone Theaters. Getting all he could out of the Windy City stage, he took the next logical step by moving to Los Angeles where, like many struggling actors before him, began working in the mailroom but not at the William Morris Agency; instead, at the Universal Studios theme park. After being involved in an auto accident, he took his combined insurance money and savings and quit that sad little job, intending to move out of the theme park and into the real world.

Livingstons first audition was for MTVs original The Real World (1992- ), but the first onscreen gig he landed was marked by a pair of lines in the feature film comedy, Straight Talk (1992) lines that were ultimately cut from the film altogether. Roles were sparse in the first few years, but 1996 marked a very rapid turning point for the eager actors bourgeoning career. Post-theme park, he was cast as a series regular in a prominent ABC vehicle for Molly Ringwald called "Townies" (1996), along with then-unknowns Lauren Graham, Jenna Elfman and Eric McCormack. Although he had a prominent role as Ringwalds boyfriend, the seaside-based sitcom vanished from the schedule after only four months, doing little for Livingstons career besides help pay the rent.

The same could not be said for his other offering that year the so money slice of Angeleno nightlife, Swingers. Written by Livingstons real-life buddy Jon Favreau, the movie was loosely based on the experiences Favreau had when he first moved to L.A. He had just broken up with a long term girlfriend and counted on his friends, Vince Vaughn and Livingston, to cheer him up. The characters both Vaughn and Livingston play in the film smooth-talking ladies man Trent and aspiring actor Rob, respectively were based on themselves including a reference to Livingstons real-life theme park work, with Rob auditioning for Goofy at Disneyland. Tapping into the swing dancing zeitgeist, Swingers literally came out of nowhere and hit the pop cultural jackpot, with its stylized dialogue quickly entering the hipsters vernacular.

Although Swingers saw a more immediate upswing for co-leads Favreau and Vaughn, Livingston enjoyed a measure of recognition for his work in the instant classic. By 1998, Livingston was no longer the bit player on television. He was cast as the loutish best friend on Thats Life (1998), a Fox sitcom that began in early March and unfortunately left the air a month later. But the following year, Livingston made good on his Swingers promise by again finding himself smack dab in the middle of a timeless classic. As the lead role in Mike Judges first live-action film, Office Space (1999) a part he won when the studios choice, Ben Affleck, went elsewhere. As the joyless cubicle-dweller Peter Gibbons, who breaks free of his shackled existence and plays out every corporate drones fantasy to say nothing of dating Jennifer Aniston Livingston brought an empathetic sense of frustration and sweetness to the role. Office Space was a hit with critics, but flopped at the box office. In its subsequent life on video/DVD, the sharp satire was unexpectedly embraced by a greater audience and turned the movie into one of the decades favorite unsung gems.

With two iconic flicks behind him, Livingston had to have felt there was no where to go but down. So he branched out, playing a variety of roles so as not to be pigeon-holed. October finally saw the release of Body Shots (1999), New Lines ensemble film about the party and hook-up culture in Los Angeles. Darker and less earnest than Swingers and shot just as Office Space was released, the film made little impact, but Livingston escaped the films rubble unscathed. In 2000, Livingston decided to flex his acting muscle by portraying Beat poet Allen Ginsberg in the independent road trip drama, Beat (2000). He also opted to try his luck once more on series television, joining ABCs hit drama The Practice (1997-2004) during the 2001-02 season as the frequently-recurring D.A. Alan Lowe. Riding high in a role created specifically for him, his first appearance in September of that year came at the same time the actor debuted with the lead role of Capt. Lewis Nixon in HBOs prestige WWII miniseries, Band of Brothers (2001).

If Livingston was already the perennial guys guy, then by 2002, he was now the girls guy as well. As novelist Jack Berger known simply as Berger on seasons five and six of HBOs Sex and the City (1998-2004), Livingston suddenly found himself an object of desire to millions of female viewers all of whom hoped Carrie Bradshaw (Sarah Jessica Parker) had finally found her soulmate in the brooding Berger. At least that was initially the case. He became a permanent part of Sex lore by turning his nice-guy image on its ear by infamously dumping Carrie with a post-it note!

Post-Berger, Livingston continued to turn out memorable performances, including that of screenwriter Charlie Kaufmans coarse, semi-fictional agent in Adaptation (2002); the tough S.W.A.T. team leader Donnie Anderson in 44 Minutes: The North Hollywood Shoot-Out (2003); and as a hard-nosed businessman trying to sanitize the old panache of Vegas casinos in The Cooler (2003). The popularity of Livingstons Berger on Sex in the City had so proven to studio executives that Livingston could charm the female contingent that he was cast as Brittany Murphys onscreen boyfriend in the summer romantic comedy, Little Black Book (2004).