Smits first attempted to parlay his small screen success into feature leads when he acted opposite Gregory Peck and Jane Fonda as an emotionally divided young Mexican general at the time of Pancho Villa's 1913 revolution in "Old Gringo" (1989), but, despite respectful notices, the film didn't do much business. Blake Edwards' "Switch" (1991), meanwhile, a middling rehash of the oft-used magical gender switcheroo, didn't even earn good reviews. Smits, though, kept busy in the acclaimed TV-movie about Fetal Alcohol Syndrome, "The Broken Cord" (ABC, 1992), and the miniseries "Stephen King's 'The Tommyknockers'" (ABC, 1993). He was the emotional fulcrum of Gregory Nava's "My Family/Mi Familia" (1995), displaying more range and aptitude than ever before in his role as a confused L.A. Latino, scarred by seeing his older brother die at the hands of a hostile gang. He also continued to win starring roles in TV-movies, such as Solomon in "Solomon and Sheba" (Showtime, 1994), and the title role in the 1995 TNT remake of "The Cisco Kid".

Returning to series TV in 1994, Smits joined the cast of the provocative and intense ABC police drama "NYPD Blue", filling the gap left by departing series star David Caruso. (Smits had actually been Bochco's initial choice for Caruso's role, but the timing had not been right for the actor the first time around.) Unlike "L.A. Law", in which his decidedly Latino role had made him TV's first Hispanic heartthrob, his "NYPD" character, Bobby Simone, was of French-Portuguese ancestry. The show rose in the ratings after his arrival, proving that good writing was more important than individual personalities, and Simone eventually won over partner Andy Sipowicz (Dennis Franz) and romanced and married fellow cop Diane Russell (Kim Delaney). After four years of playing Simone (and methodically snagging best actor Emmy nominations), however, Smits opted out of the show. The producers responded by killing off his character from complications of a heart transplant rather than leave the door open for a second act.

Smits enjoyed prominent roles in three features debuting in early 2000. He joined an impressive array of talent (i.e., Mel Gibson, Milla Jovovich, Gloria Stuart) for Wim Wenders' fabulous-looking thriller, "The Million Dollar Hotel", which debuted at the Berlin Festival. Despite its superb craftsmanship, the film's underdeveloped and not very interesting story kept US distributors on the sidelines, perhaps awaiting its European fate. "Bless the Child" cast him as a police detective who helps a nurse stop a Satanist plot to carry out a Biblical prophecy against her six-year-old niece. Paramount hoped for great things from its teaming of Kim Basinger (in her first role since "L.A. Confidential") with Smits and that audience enthusiasm for supernatural thrillers (a la "The Sixth Sense") had not peaked. Always a champion of quality Latino-themed projects, he also starred as washed-up boxer Arturo Ortega, trying to mend his broken dreams by training his three sons in "Price of Glory".

Smits was next cast in the Star Wars prequel "Episode II: Attack of the Clones" (2002) as Senator Bail Organa, the future foster father of Princess Leia. He also signed on to reprise his role in an expanded capacity for the third installment, "Star Wars: Episode III - Revenge of the Sith" (2005), fulfilling the character's promised destiny. Meanwhile, Smits took on Shakespeare in as Orsino in a 2002 Broadway performance of "Twelfth Night." He then joined the cast on the ever-popular “West Wing” in 2004 as Rep. Matt Santos, an idealistic Democrat who vies for his party’s nomination for the presidency, and appeared in the ensemble of the HBO race relations telepic "Lackawanna Blues" (2005).