His first break was in 1990, when he joined the staff of the NBC sketch comedy show “Carol & Company,” starring Carol Burnett. From there, he joined the staffs of network comedy powerhouses of the day – ABC’s “Home Improvement,” and CBS’ “Murphy Brown.” It was on “Brown,” the sharp, politics and news satire starring Candace Bergen, that Tolan won his first Emmy award, one of his two nominations for the show.
Tolan also joined the revered and cult favorite HBO comedy, “The Larry Sanders Show,” the biting glimpse behind the scene of a fictional talk show, created by and starring Gary Shandling. Tolan won his second Emmy for writing the poignant series finale, featuring guest Jim Carrey, in 1998. He was nominated five other times for the show.
Tolan continued to work in television for the next few years, as a writer on ABC’s “Ellen,” with Ellen DeGeneres, and the short-lived “Buddies,” starring Dave Chappelle before he reached superstardom. He also created “The George Wendt Show,” which ran only seven episodes, also on ABC.
Tolan began his foray into movies at that time, penning screenplays for “My Fellow Americans,” in 1996, a comedy starring Jack Lemmon and James Garner as ex-presidents, and “What Planet Are You From,” a comedy by director Mike Nichols, starring Garry Shandling. Those modest showings were followed by the blockbuster comedy “Analyze This,” in 1999, its sequel “Analyze That” in 2003, and “Bedazzled,” in 2000, all for director Harold Ramis. He also wrote “America’s Sweethearts,” starring Billy Crystal and Julia Roberts, released in 2001, following it with “Stealing Harvard.”
In 2001, he forged a creative partnership with comedian Denis Leary to produce the highly original ABC television series “The Job,” a cop show which broke from the trend of police procedural and focused almost entirely on the characters and their personal lives. The show also broke from form with its half-hour running time and took the edgy-looking hand-held shooting style pioneerd by "NYPD Blue’s" Stephen Bochco, to new heights. Tolan played a bit part, as the character Sean, in the episode entitled, “Sacrilege.” Despite a critical and cult following, the show was not a ratings hit, but Tolan and Leary vowed to work together again, and followed up their efforts with “Rescue Me,” a look behind the scenes at a New York City firehouse. With its portrayal of firefighters as both heroic and deeply flawed, many still disturbed by lingering thoughts of 9/11, the show was a critical and rating success.
On top of the producing and directing duties for the show, Tolan continued to work in feature films, including in 2005 the romantic comedy “Just Like Heaven,” starring Reese Witherspoon and Mark Ruffalo, and 2005's “Guess Who,” a comic reversal of the racial drama “Guess Who’s Coming to Dinner.” He also wrote the screenplay for “The Smoker,” to be directed by Richard Linklater and star Natalie Portman and Tobey Maguire.