Sarsgaard made his big screen debut in 1995 with a role as one of the murder victims in Tim Robbins' gripping prison drama "Dead Man Walking". He was featured three years later in "The Man in the Iron Mask" with a pivotal if small role as the doomed Raoul, son of Athos (John Malkovich) and suitor of Christine (Judith Godreche) whose death on the frontlines of war (sent there purposely by Leonardo DiCaprio's lusty and cruel Louis XIV) leads to a monumental mutiny led by three of the four Musketeers. Roles in the grittier independents "Another Day in Paradise" (1998) and "Desert Blue" followed, with the charismatic Sarsgaard turning in strong performances with little screen time.

With previous film work including turns as innocent victim and noble hero, Sarsgaard switched gears and in 1999 essayed a disturbing co-starring role in Kimberly Peirce's powerful "Boys Don't Cry". This acclaimed and moving feature was based on the 1993 murder of Teena Brandon, a young woman living as a man in Falls City, Nebraska. Sarsgaard's talents were showcased in the film by his appropriately intense and unnerving portrayal of John Lotter, the unstable friend convicted of raping and murdering 'Brandon' after her identity as a biological female was exposed. He impressed in this demanding and harrowing role, conveying both Lotter's winning charm as well as the underlying violence (evidenced by the character's erratic outbursts and the alarming brutality of the attack on Teena Brandon.) He subsequently co-starred with Jennifer Lopez and Vince Vaughn in the thriller "The Cell" and with Rupert Everett and Kathy Bates in P J Hogan's "Unconditional Love" (both lensed 1999).

Sarsgaard snared the lead role in director Wayne Wang's erotic drama "The Center of the World" (2001), playing a successful computer wiz whose technological immersion has left him devoid of human connection, until he meets a rock band drummer (Molly Parker) and they escape on a three-day trek to Las Vegas to explore the limits of their sensuality. He also had a noticeable turn as slacker Jimmy the Finn in the twisty indie crime drama "The Salton Sea" (2002), supported Harrison Ford and Liam Neeson as a cowardly nuclear reactor technician in the Soviet submarine thriller "K-19: The Widowmaker" (2002) and resurfaced in the urban crime drama "Empire" (2002) as the slick stock market investor who draws drug dealer John Leguizamo into a world of trouble.

Sarsgaard would have his breakthrough performance in writer-director Billy Ray's invovling yet understated taken-from-the-headlines drama "Shattered Glass" (2003). In a well-measured story of journalistic ethics woven around the true case of wunderkind reporter Stephen Glass (Hayden Christensen) who fabricated several articles for major publications, Sarsgaard's performance as New Republic editor Chuck Lane, who serves as the story's moral compass. The actor's realistic, uncompromisign portrayal earned him his biggest round of critical praise to date, including a Golden Globe nomination for Best Performance by an Actor in a Supporting Role in a Motion Picture. He then teamed with another "Star Wars" alum, actress Natalie Portman, and writer/director/star Zach Braff for the charming, off-kilter indie dramedy "Garden State" (2004), in which he deftly played Braff's eccentric high school buddy.

Uncharacteristicaly, the typically restrained actor seemed a bit overzealous in his next film, playing a Southern lawyer in the atmospheric thriller "The Skeleton Key" (2005) opposite Kate Hudson, but provided a welcome presence as a U.S. air marshal who attempts to alternately calm, humor and restrain and frantic mother (Jodie Foster) who believes she's lost her daugther on an airline in "Flightplan" (2005). In "Jarhead" (2005), director Sam Mendes' insightful adaptation of former U.S. Marine Anthony Swofford's bestselling memoir of his service during the 1990 Gulf War in Iraq, Sarsgaard was pitch-perfect as Troy, scout to sniper Swoff (Jake Gyllenhaal) and a die-hard member of the Marine Corps who hopes to prove himself in combat, as desperate to stay in the war as Swoff is to escape.