Eventually, he began landing roles, making his feature debut as a crooner in Woody Allen's nostalgic "Radio Days" (1987), the baby-faced performer segued to series TV as an incompetent public relations maven in the short-lived 1987 CBS sitcom "Take Five.” He marked time in such forgettable films like "The Allnighter" (1987) before landing his first major part as an over-worked medical student alongside future production partner Matthew Modine in "Gross Anatomy" (1989). After another small turn in "Fat Man and Little Boy" (also 1989), he joined the down-and-dirty world of B-movies in "Full Fathom Five", the Roger Corman-produced, cheapie "Red October" rip-off, before enjoying a better showcase in "Back to Back" (both 1990), as one of two brothers trying to clear their father's name.

Field had the good fortune of hooking up with Victor Nunez for the director's award-winning character study "Ruby in Paradise" (1993). Playing Mike McCaslin, the literate, dreamy nurseryman and major love interest of Ashley Judd's title character, the actor received great reviews and seemed poised for bigger and better things. Instead, Field took time off to study directing at the American Film Institute. He made several short films including "Too Romantic" (1992), the Sundance-screened "Smoking" (1993, co-directed with Matthew Modine), "Delivering" and "When I Was a Boy" (also 1993) and "Nonnie and Alex,” which earned an honorable mention at the 1995 Sundance Film Festival.

Resuming his acting career, he was cast alongside off screen pal Eric Stoltz in "Sleep With Me" (1994), playing a politically incorrect guy who says exactly what's on his mind. Field offered a fine turn as the petty thief son of a big-time criminal (Ben Gazzara) in the moderately well-received "Farmer & Chase" (1995) and enjoyed a box-office success with the blockbuster "Twister" (1996), his first collaboration with director Jan De Bont. While "Twister" had mass appeal, he was better showcased in "Walking and Talking", portraying Anne Heche's hunky, nervous fiancé.

While biding his time in search of the perfect project with which to make his feature directorial debut, Field remained busy in front of the cameras, enjoying his most prolific year yet with three 1999 July releases. While he had small roles in two big-budget studio pictures, De Bont's disappointing "The Haunting" and Stanley Kubrick's highly-anticipated, salacious swan song "Eyes Wide Shut,” Field fared far better in the edgy independent "Broken Vessels" delivering arguably the best performance of his career as a slow-burning demon of a paramedic who seemingly thrives in the pressure cooker atmosphere of life behind the wheel of an ambulance. As drug abuse takes its toll and his character spirals out of control, he eschewed an over-the-top approach, choosing instead just the right quiet notes to add realism to his performance. Capping off this banner year, he returned to series TV as a regular on ABC's "Once and Again,” playing the partner to Billy Campbell's Rick Sammler.

Field had another watershed year in 2001. While he was wrapping up his two-year stint on "Once and Again,” he had managed to find that perfect project for his debut film. Adapting a short story by Andre Dubus, Field co-wrote (with Rob Festinger) and directed the haunting, visually appealing and well-acted "In the Bedroom". Focusing on the after effects of a tragedy on the lives of a seemingly close-knit Maine family, "In the Bedroom" screened at the 2001 Sundance Film Festival to a deservedly rapturous reaction. Anchored by stellar lead performances by Sissy Spacek and Tom Wilkinson and featuring strong support from Marisa Tomei, Nick Stahl and William Mapother, the film immediately sparked Oscar talk. Released in the fall to glowing reviews, the movie allowed Field to take his place as a potent new voice in American cinema.

It was five years before Field directed another movie, with nothing—no writing or acting gigs—to tide him over in between. In 2004, well after the attention and adulation he received for “In the Bedroom” had died down, Field got to work on his next project, “Little Children” (2006), a darkly satiric take on suburban life and the American way, based on the acclaimed novel by Tom Perrotta (who also co-authored the script). The story focused on a stay at home mom, Sarah (Kate Winslett), on the outs with the other moms at the playground engaged in an illicit affair with an ex-jock, Brad (Patrick Wilson), rebelling against his wife (Jennifer Connelly) who wants him to get off his duff and become a big time lawyer. Thrown into the mix is a pedophile (Jackie Earle Haley) released from prison and trying to get his life with the help of his mom (Phyllis Somerville), who tries to set him up with a nice girl (Jane Adams). The film earned mostly rave reviews and numerous award nominations, including a Best Adapted Screenplay nod for Field at the 79th Annual Academy Awards.