The lanky Robbins made his TV debut opposite Helen Hunt in the movie "Quarterback Princess" (CBS, 1983) and landed a small role in a Martin Scorsese-directed episode of Steven Spielberg's "Amazing Stories" entitled "Mirror, Mirror" (NBC, 1986). Following his feature debut in "No Small Affair" (1984), he delivered a memorable turn as the show tune-singing driver in Rob Reiner's "The Sure Thing" (1985), cultivating a lasting association with that film's star John Cusack, before showing up on the periphery of the blockbuster "Top Guns" (1986). His first lead, ominously, was in the notorious flop "Howard the Duck" (also 1986), but the lucky actor survived it to work again, playing Jodie Foster's former boyfriend who protects her from a twisted John Turturro in the unheralded, eccentric, early-60s civil rights drama "Five Corners" (1987), scripted by John Patrick Shanley. He also reunited with Cusack as a reluctant video director for "Tapeheads" (1988), a picture which marked his first songwriting credit.

The turning point in his career—and life—was also the fulfillment of a lifelong dream. His role as the goofy, garter-wearing 'Nuke' LaLoosh, the baseball innocent coached by Kevin Costner and Susan Sarandon in Ron Shelton's "Bull Durham" (also 1988), allowed him to show off his pitching prowess, throwing a fastball clocked at the very respectable major-league speed of 85 miles per hour ("But I had absolutely no control"). Robbins met Sarandon at the audition in Los Angeles, and the pair began a relationship during filming that has endured to date, If the film had one downside, it was in creating a misconception of him as a sort of male bimbo, an image he would eventually dispel after marking time with "Miss Firecracker" and Terry Jones' comedy "Eric the Viking" (both 1989) and stealing the show from the manic Robin Williams in "Cadillac Man" (1990). He broke through once again as a tormented Vietnam veteran in the spooky "Jacob's Ladder" (1990) and then played the first of his self-styled "trilogy of assholes", the racist boss in Spike Lee's "Jungle Fever" (1991).

With his soft, unthreatening looks and easy manner, Robbins can make a killer seem sympathetic, which he managed to do in Robert Altman's "The Player" (1992), As insecure studio executive Griffin Mill, a modern-day Faust, he smiled calmly while his colleagues dropped like flies and he climbed over their Armani-clad corpses to the top of the back-lot heap. His deceptively wicked performance earned best actor awards form both Cannes and the Golden Globes. Starring in his feature directorial/screenwriting debut, the "mockumentary" "Bob Roberts" (1992), he portrayed a right-wing, folk-singing senatorial candidate, spouting sound-bite local yokelisms and creating a frighteningly real portrait of a perfectly respectable, profoundly crooked politician ("That was probably the work I'm most proud of"). Reuniting with Altman for "Short Cuts" (1993), a resetting of Raymond Carver's collection of short stories, Robbins provided much of the humor with his somewhat caricatured portrayal of an egocentric Los Angeles cop. However, his third film with Altman, the fashion industry comedy "Ready to Wear (Pret-a-Porter)" (1994), earned the director some of the most scathing reviews of his career.

In 1994, Robbins let his gawky charm work overtime as an idealistic bumpkin who unwittingly becomes a corporate stooge in the Coen brothers' stab at mainstream accessibility, "The Hudsucker Proxy,” and also tried his hand at a romantic lead (to mixed reviews) opposite Meg Ryan in "I.Q.", but in "The Shawshank Redemption" he gave a low key and exquisitely modulated performance that was easily his best of the year. His tour de force portrayal of the mild-mannered, unjustly imprisoned banker, coupled with that of Morgan Freeman playing the seasoned lifer who befriends him, significantly elevated the well-crafted but overly-long and somewhat predictable jailhouse drama adapted from a novella by Stephen King.

Chaos, the production company Robbins formed in 1993 bore its first fruit with the death penalty drama "Dead Man Walking" (1995). For this true story, the sophomore director used the same director of photography (Roger Deakins) who had so effectively captured prison life for "The Shawshank Redemption". Sarandon played a nun acting as spiritual counselor to a death row murderer (Sean Penn) and took home the Best Actress Oscar. Though the film was ostensibly a plea against the death penalty, Robbins' treatment of the subject matter was so even-handed that many capital punishment advocates believed the director was in their camp. For his efforts, he garnered a well-deserved Best Director Academy Award nomination and proved that his relationship with Sarandon could easily survive "six horrible days" incurred during filming.

Just as people were thinking he was too serious, Robbins crossed them up with his next acting project, starring opposite Martin Lawrence in the buddy-pic "Nothing to Lose" (1997). As a hotshot advertising executive gone 'round the bend, he turned the tables on Lawrence's carjacker by taking him hostage. Unfortunately, audiences found "Nothing to Lose" nothing to laugh at, and the Steve Oedekerk film fizzled at the box office. After an 18-month hiatus to concentrate on fatherhood, Robbins was back on the screen in 1999, contributing a cameo as the President in "Austin Powers II: The Spy Who Shagged Me" and once again exploring his dark side in "Arlington Road", a thriller echoing the Oklahoma City bombing and raising hard questions about domestic terrorism.

Robbins came by his political conscience honestly enough, inheriting it from his peace and civil-rights activist father. He remembered his sister getting arrested for protesting the Vietnam War and his parents telling him, "It took courage for your sister to do this." In keeping with his sense of social responsibility, his third time in the director's chair, "Cradle Will Rock" (1999), resulted in his most ambitious film to date, a deeply felt homage to a time when passionate commitment, not dreams of profit or celebrity, drove artistic activity. Taking the Federal Theater's polemical 1936 musical drama "The Cradle Will Rock" as a starting point, Robbins evoked the dynamic cultural landscape during a tumultuous and exciting period. Though it may have erred in its tendency toward caricature when portraying certain famous individuals, "Cradle Will Rock" was that rare Hollywood-backed venture, a $32 million picture about committed people and a testament to Robbins' will to make movies that ran counter to the mainstream.

After the triumph—artistically if not commercially—of "Cradle," Robbins eased into a succession of character roles in mid-level movies, playing an astronaut in Brian de Palma's "Mission to Mars" (2000), a Bill Gates-esque software manufacturer in the thriller "Antitrust" (2001) and a scientist who discovers a feral man in the off-kilter comedy "Human Nature" (2002). He also reassumed the reigns at the Actors' Gang, returning as artistic director in 2001 and spearheading a renewed, ambitious production schedule that frequently employed his many talents: he directed a new production of "Mephisto," starred with Helen Hunt in the Los Angeles production of the 9/11-themed play "The Guys" and saw a revival of "Alagazam," a play he co-wrote with Adam Simon. When he returned to acting on the big screen in a mainstream project—Jonathan Demme's "Charade" remake "The Truth About Charlie" (2002)—it was also as a supporting player, stepping into the calculating role of Mr. Bartholomew, in which he freely and gleefully borrowed from Walter Matthau's original characterization, defying Demme's edict not to reference the original film.

Robbins starred in one of his most compelling performances to date when he was cast in director Clint Eastwood's "Mystic River" (2003), playing Dave Boyle, a man connected to the murder of the daughter of his childhood friend (Sean Penn) by a series of circumstances and forced to confront the demons of his own past that threaten to destroy his marriage and any hope he may have for a future. Robbins received an Academy Award as Best Supporting Actor for his performance, as well as Golden Globe for Best Supporting Actor in a Motion Picture and a Screen Actors Guild Award.

Robbins had an amusing cameo as a public TV anchor in the Will Ferrell comedy "Anchorman: The Legend of Ron Burgandy" (2004) before going on to a compelling supporting role as the shell-shocked survivalist Ogilvy who provides shelter to a desperate dad (Tom Cruise) and his daughter (Dakota Fanning) during a horrific alien invasion in Steven Spielberg's riveting remake of the sci-fi classic "War of the Worlds" (2005). In a lighter vain, he played the father of three children who, during his brief absence, find their family home rocketed into space and under attack by Zorgons when the board game "Zathura" (2005) comes to life. Returning to potential Oscar territory, Robbins stepped into different shoes in “Catch a Fire” (2006), playing a colonel in the Police Security Branch who strives to maintain order in apartheid-era South Africa. He confronts a loving husband and father (Derek Luke) who works at an oil factory where an explosion linked to the outlawed African National Congress occurs. Though unconnected to events, the accused man nonetheless joins the rebel group to fight against the injustice that occurred to his family during his arrest and to his country at large. Robbin’s performance as the evil security chief forced the actor into the position of understanding apartheid through the white’s perspective, allowing him a more nuanced and human portrayal. Nonetheless, Robbins kept to his left-leaning politics in staunchly opposing the racist system he protested against in the 1980s and 1990s.