Such lauded performances as Lindo gave in "Joe Turner's Come and Gone" and "Malcolm X" should have opened the floodgates for film and theater offers, but pickings remained extremely slim for the talented performer. Fortunately Lindo had writer-director Lee in his corner. In 1994, he starred in Lee's quasi-autobiographical "Crooklyn" as Woody Carmichael, the idealistic jazz musician father of an African-American clan in 1970s Brooklyn. Lindo created the character of an enormously appealing man undermined by a lack of self-discipline and irresponsibility. He rejoined the director for "Clockers" (1995), a gritty true-life crime story, playing Rodney, a charismatic yet sociopathic coke kingpin. The film received generally respectful reviews with particularly glowing kudos for Lindo.
That year marked a turning point for Lindo as he began a series of supporting roles in high-profile genre films that were not necessarily Black-identified. He joined the resurgent John Travolta for the well-received, black comedy crime flick "Get Shorty" (1995), playing a drug dealer with cinematic aspirations, and worked with him again in the John Woo-directed thriller "Broken Arrow" (1996). Neither "Feeling Minnesota", which cast him as a gangland boss, nor Ron Howard's "Ransom" (both 1996), in which he appeared as an almost unrealistically upbeat FBI agent, broke any new ground for him, but Danny Boyle's "A Day Less Ordinary" (1997) offered a change-of-pace as an angel, who along with fellow spirit Holly Hunter enjoyed some choice comic moments playing Cupid for Cameron Diaz and Ewan McGregor.
Although relegated to supporting turns in features, Lindo landed meaty leading roles in TV-movies. His outstanding portrayal of baseball legend Satchel Paige anchored HBO's "Soul of the Game" (1996), presenting the famed pitcher as a man of considerable business savvy who carefully calculated his down-home country boy image for public consumption. In TNT's "Glory & Honor" (1997), he brought soul and dignity to polar explorer Matthew Henson, whose contributions to Robert Peary's nine attempts on the North Pole have gone largely unmentioned by history. Showtime's "Strange Justice" (1998) allowed the actor to emotionally capture future Supreme Court Justice Clarence Thomas as a self-righteous creature of ambition. He also created and executive produced both the Independent Film Channel's "Delroy Lindo on Spike Lee" (1999) and "Conversations With Charles Burnett" (Showtime, 2000, which he directed). As the conflicted foreman of "The Cider House Rules" (1999), Lindo offered arguably the most multi-layered performance of his film career delineating a man who on the surface seemed good but who harbored a dark and disturbing secret. He then segued to action films as another gangland boss in "Romeo Must Die" and a detective matching wits with master car thief Nicolas Cage in the remake of "Gone in 60 Seconds" (both 2000).
In 2001, Lindo starred in several diverse film roles. After playing a space traveling cop navigating wormholes in pursuit of a murderer (Jet Li) in the martial arts sci-fi action flick, “The One,” he appeared alongside luminaries Robert Redford, James Gandolfini and Mark Ruffalo in the ham-handed military prison drama “The Last Castle.” He next appeared in David Mamet’s “Heist,” another in a line of crime dramas from the former playwright depicting backstabbing thieves spouting clipped dialogue laden with sharp profanity and wearied machismo. Lindo returned to television, playing a mentally retarded man who meets same (Kirstie Alley) at an institution and starts a family with her over the objections of authorities in the made-for-TV movie, “Profoundly Normal” (CBS, 2003). After playing the creator of a ship sent to detonate a nuclear weapon inside the Earth’s core in the dreadful sci-fi actioner, “The Core” (2003), Lindo appeared in the big budget adventure, “Sahara” (2005), starring Matthew McConaughey, Steve Zahn and Penelope Cruz.
Lindo switched over to the small screen for a spell, appearing in “The Exonerated” (2005), a made-for-Court TV movie adapted from a play written by Jessica Blank and Erik Jensen about six wrongly accused people whose death row sentences are overturned through the hard work of dedicated lawyers. The stories—taken from real-life cases and culled from mountains of court testimony, interviews and letters—were devoid of any political arguments for or against the death penalty, allowing the stories of the wrongly accused to be told with maximum emotional impact. Lindo next gave a standout performance in the award-winning cable movie, “Lackawanna Blues” (HBO, 2005), playing Mr. Luscious, a one-armed man with a strange past who, along with an assorted cast of characters, lives in a boarding house run by a strong and dignified woman (S. Epatha Merkerson). After a small role as a bail bondsman in “Domino” (2005), a true-to-life tale about a former fashion model turned drug-abusing bounty hunter (Keira Knightley), Lindo was cast in his first regular series role, playing a soon-to-be retired FBI agent brought in by an independent investigator (Jeremy Sisto) to help solve a kidnapping involving the teenaged son of a wealthy family (Dana Delany and Timothy Hutton).