While Logue's career advancements are mostly due to his film efforts, he began his work on the small screen, with numerous guest stints on series, supporting parts in TV-movies and regular roles on failed series. Logue started out with a role in the Mike Newell-directed miniseries "Common Ground" (CBS, 1990), about the desegregation of Boston schools, and followed up with a turn as a suspected bomber in the 1991 "American Playhouse" (PBS) production of the biographical drama "Darrow.” In 1993, the actor took a more instrumental role in the CBS drama "Labor of Love: The Arlette Schweitzer Story", playing the husband of a woman (Tracey Gold) who enlists the help of her mother (Ann Jillian) to conceive and carry the couple's child. He was also featured that year as an early AIDS victim in the HBO drama "And the Band Played On.” Guest roles on "The X-Files" (Fox) and "Almost Home" (ABC) showcased Logue's range, with roles as an FBI agent and pop music idol respectively.

In 1994, his talked-about stint as Jimmy the Cabdriver began. Working with fellow Harvard graduate Jesse Peretz, Logue created this often misinformed but always interesting (to viewers, not his passengers) video-dissecting, pop-culture commenting personality. Greasy-haired with thick black-framed glasses, Logue was virtually unrecognizable, appearing much older than his not-quite thirty years. A particularly inspired "Jimmy the Cabdriver" spot featured Logue recreating Alanis Morissette's "Ironic" video, with a car full of Jimmys replacing the car full of Alanises with different clothes and personas. Logue's next television project would mark his debut as a series regular, starring on the short-lived hospital drama "Medicine Ball". He followed this series' quick demise with a regular role the following year in the similarly-fated CBS law-enforcement comedy "Public Morals". These disappointments didn't stall the actor's career as he was already making headway on the big screen. A 1998-1999 recurring role as an Assistant District Attorney on ABC's "The Practice" joined other guest appearances in keeping him a familiar face to television viewers, but nearly all of Logue's post-1995 work was in film.

The spy thriller "Sneakers" (1992) marked Logue's feature acting debut, and within eight years the prolific performer would have nearly two dozen films to his credit. Supporting turns in "Gettysburg" (1993) and "Little Women" (1994) followed, and Logue marked his first starring role with a turn in the independent thriller "The Crew" (also 1994). He racked up supporting credits in such disparate fare as "3 Ninjas Knuckle Down" (1995) and "Diabolique" (1996). Independents like "Baja" and "The Grave" (debuted on HBO) offered Logue meatier parts in 1996, the same year that he reached a wide audience with a turn as a junior talent agent in the popular feature "Jerry Maguire.” His deft portrayal of varied characters (the grief-stricken father of a slain child in "Eye For an Eye" and an Anglo-Hawaiian slacker in "The Size of Watermelons" just two examples from 1996 alone) pointed to the versatility that would win the actor a bevy of enviable character roles. In 1997 Logue continued to work in independent film, reuniting with Jesse Peretz on the director's feature debut "First Love, Last Rites". A larger role in the supernatural actioner "Blade" won Logue notice and acclaim, and he would stay busy through the end of the 1990s with memorable supporting performances. He played a jilted groom turned parish priest in the Julia Roberts-Richard Gere romantic comedy "Runaway Bride" (1999) and returned to the driver's seat as a zany chauffeur in the hairstyle competition-set comedy "The Big Tease" (2000).

Logue had a productive year in 2000, following up an underdeveloped role in John Frankenheimer's "Reindeer Games" with a Sundance victory, winning the festival's Special Grand Jury Prize for Outstanding Performance for his portrayal of unlikely lady-killer Dex, an average-looking, unsuccessful and overweight man whose life philosophy, "The Tao of Steve,” makes him a hit with nearly every woman he sets his sights on. The film, directed by newcomer Jennipher Goodman, was a surprise hit of the festival due in no small part to Logue's dynamic and engaging performance. That same year he appeared in the Berlin Film Festival hit "The Million Dollar Hotel,” directed by Wim Wenders (which wasn't released theatrically until 2001), and starred alongside Cyndi Lauper and Christopher Walken in yet another independent feature, "The Opportunists." No end to Logue's big screen assault seemed in sight, with roles in the fact-based hacker thriller "Takedown" (2000), Mel Gibson's Revolutionary War drama "The Patriot" (2000), the Ben Affleck/Charlize Theron caper "Reindeer Games" (2000) and the clever indie cult heist drama "Comic Book Villains" (2001).

Shifting to the small screen, Logue starred as the post-modern family man Sean Finnerty, a too-young-dad who struggles with responsibility, in the sitcom "Grounded For Life" (Fox, 2000-2002, The WB, 2002-2005). His feature film career continued unabated, with roles as a corrupt cop in the slippery con drama "Confidence" (2003) and as a stage actor playing cartoonist Harvey Pekar in the acclaimed indie "American Splendor" (2003). Logue stole nearly every scene he was in when he played Mark Ruffalo's morally challenged best friend in the "Ghost"-like romantic comedy "Just Like Heaven" (2005) opposite Reese Witherspoon. He next costarred alongside Edward Burns in “The Groomsmen” (2006), a dramedy focused on five friends reminiscing about old times and fretting about the impending doom of married life. In a return to television, Logue landed a starring role in the midseason pickup “The Knights of Prosperity” (ABC, 2006- ), a high-concept comedy about a group of blue collar guys fed up with their meager lives who decide that their only hope is to rob Mick Jagger’s apartment. Logue played a janitor who assembles a motley crew of likeminded losers to pull of the ridiculous heist.