Ruffalo had minor roles in films like The Dentist (1996), the low-key crime comedy Safe Men (1998) and Ang Lee's acclaimed Civil War Western Ride with the Devil (1999). Through a chance meeting with striper Kenneth Lonergan, Ruffalo began collaborating with Lonergan and appeared in several of his plays, including the original cast of This is Our Youth (1998), which led to Ruffalo's role as Laura Linney's troubled, aimless drifter brother Terry in Longeran's acclaimed, Academy Award-nominated 2000 film You Can Count on Me. He received favorable reviews for his performance in this film, often earning comparisons to the young Marlon Brando, and won awards from the Los Angeles Film Critics Association and Montreal World Film Festival.
This led to other significant roles, including the films XX/XY (2002), Isabel Coixet's My Life Without Me alongside Sarah Polley (2003), Jane Campion's In the Cut alongside Meg Ryan (2003), Michel Gondry's Eternal Sunshine of the Spotless Mind (2004), and We Don't Live Here Anymore (2004), which is based upon two short stories written by Andre Dubus. He appeared opposite Tom Cruise as a homicide detective in Michael Mann's acclaimed crime-thriller Collateral (2004). More recently, Ruffalo has appeared as a romantic lead in "chick flicks" such as View From the Top (2002), 13 Going on 30 (2004), Just Like Heaven (2005) and Rumor Has It (2005).[4] In 2006, Ruffalo starred in Clifford Odets's Awake and Sing! at the Belasco Theater in New York, for which he was nominated for a Tony Award for Best Featured Actor in a Play. In March, 2007, he appeared in Zodiac as SFPD homicide inspector Dave Toschi, who ran the investigation to find and apprehend the Zodiac killer from 1969 through most of the 1970s. October 2007 saw Ruffalo play divorced lawyer Dwight Arno, who accidentally kills a child and speeds away, in Terry George's film Reservation Road based on the same titled novel by John Burnham Schwartz.
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