Often typecast as thugs, Mafia henchmen and police officers but just as effective as gentle giants and more cerebral characters, Starr was rarely at a loss for work. A role on Broadway in "Requiem For a Heavyweight" and turns in the features "The Last Dragon" and "The Protector" came in 1985. Appearances in the hit films "The Money Pit" (1986), "Radio Days" (1987) and "Punchline" (1988) as well as several others took him through the 1980s, finishing up the decade with 1989 turns in "Born on the Fourth of July" (featured alongside his brother, fellow actor Beau Starr) "Lean on Me", "Uncle Buck" and "Last Exit to Brooklyn". Starr started the 1990s with featured turns in the acclaimed organized crime dramas "GoodFellas" and "Miller's Crossing", and acted on television in the fact-based CBS desegregation miniseries "Common Ground" (all 1990). He returned to mob films with a role in the 1930s NYC-set gangster feature "Billy Bathgate" and gave a memorable supporting performance the following year, playing a bad guy who surprisingly falls in a battle with Kevin Costner's comparably tiny title character in "The Bodyguard" (1992).

In 1993, Starr was featured in the comedy "Mad Dog and Glory", with a sharply played comedic turn as Bill Murray's bodyguard that steered clear of gangster stereotypes. The following year he racked up a number of memorable if buffoonish film credits, taking beatings from Chris Elliot in "Cabin Boy" and Steven Seagal in "On Deadly Ground" and playing the man on the trail of two lovestruck idiots in the Farrelly brothers hit "Dumb and Dumber". He broke away from his usual roles in Tim Burton's "Ed Wood", playing Georgie Weiss, a slick producer who gives Wood his first green light. That same year Starr became a television regular with a role on the Fox sitcom "Hardball", playing veteran catcher and family man Mike Widmer. While the down-to-earth character was a good fit for the actor, the show suffered from low ratings and was dropped from the lineup. Also on the small screen that year, Starr had a memorable guest role on "Frasier" (NBC), playing the adult incarnation of a bully who tormented the Crane brothers in their youth.

Starr stayed busy through the latter half of the 90s with more character parts. He was featured as police officers in 1995's "Clockers" and "A Pyromaniac's Love Story" and 1996's live-action/animated children's adventure "James and the Giant Peach", playing a shady cop, a New Age-inspired officer and a friendly patrolman, respectively. From 1996-1997, he co-starred on the gritty CBS police drama "EZ Streets" as Mickey Kinnear, the brawn behind crime boss Jimmy Murtha (Joe Pantoliano). 1997 saw the actor take his first feature starring role in the independent comedy "The Deli". Here he starred as Johnny, a store owner on a losing streak who has to come up with the prize money for a winning numbers bet he neglected to enter for his mother. With a cast full of up and comers (Matt Keeslar, Gretchen Mol) as well as veteran character players (Burt Young, Jerry Stiller), "The Deli" was a charming and genuinely funny film, and proved that Starr could carry a movie as well as excel in supporting parts. 1998 saw the actor return to character roles, with a featured turn in Brian De Palma's suspenseful "Snake Eyes". Featured roles in Sidney Lumet's remake "Gloria" and Spike Lee's harrowing "Summer of Sam" followed in 1999.

A veritable constant in film, Starr began racking up more significant TV parts as the 90s drew to a close. A 1998-1999 two-episode recurring role on "Martial Law" (CBS) was followed by a similar double stint on the network's "Falcone" (which reteamed him with "EZ Streets" co-star Jason Gedrick and writer-producer Robert Moresco) in 2000. Between these appearances, Starr found time to star alongside Gene Wilder in the A&E original movies "Murder in a Small Town" and "The Lady in Question", playing the police detective teamed up with Wilder's Broadway director-turned-private investigator in the 1930s Connecticut-set mysteries. Fall of 2000 marked the actor's return to regular series work, with a co-starring role as Kenny, a quiet, quirky and overqualified bowling alley employee inherited by the eponymous new owner on NBC's "Ed". "Ed" was an exceptionally likable series, and proved a breakout hit of the new season. Its popularity gave hope of a strong future for the series, and a chance to see Starr develop his somewhat mysterious character further as the season progressed.