After appearing as Billy Douglas on the soap opera One Life to Live (1992–1993) and making his feature film debut in Crimson Tide (1995), he came to prominence in the late 1990s with starring roles in I Know What You Did Last Summer (1997), 54 (1998), Playing by Heart (1998), and Cruel Intentions (1999).

Outside of film, Phillippe appeared in the lead role of Bob Lee Swagger on USA Network's Shooter (2016–2018) and reprised his portrayal of Dixon Piper in the Peacock adaptation of MacGruber (2021).

[2] His mother, Susan, ran a day care center in the family's house; his father, Richard Phillippe, was a chemist.

It was a success among its intended teenage audience, cementing Phillippe's ability to play characters that require sex appeal.

In the years following, he appeared in the crime drama The Way of the Gun, starred as a famed software engineer in the thriller Antitrust, and co-starred in Robert Altman's Gosford Park, which was nominated for the Oscar for Best Picture.

[11] Phillippe's next role was in the thriller Breach, in which he played FBI investigator Eric O'Neill opposite Chris Cooper.

[12] He then starred in Chaos, in which he plays a police officer; Five Fingers, a drama set in Morocco; Kimberly Peirce's Iraq war film Stop-Loss; and the futuristic Franklyn.

Next up for Phillippe was a rare comedic role as Lt. Dixon Piper in MacGruber, a film based on the Saturday Night Live (SNL) skit of the same name.

[24] The movie focuses on a group of young men from Detroit whose attempt at a diamond heist goes awry and brings them into conflict with a mob boss.

[30] Starting in November 2011, Phillippe spent several months filming a 10-episode arc on the fifth and final season of the critically acclaimed TV show Damages.

The movie features Phillippe as an American man who travels to Puerto Rico with his wife to adopt an orphan from Haiti.

It is based on the Australian series of the same name, with Phillippe playing a family man who becomes a prime murder suspect after he discovers the body of a child.

[49] Phillippe, Breckin Meyer, Seth Green, and David E. Siegal run a production company called Lucid Films.

[7] The comedy, Heavy and Rolling, tells the story of a Manhattan towncar driver who assumes different identities as he moves towards madness.

[50] Phillippe also served as executive producer and narrator on Isolated, a documentary that follows five surfers as they travel to remote New Guinea in search of untouched waves.

[53][54] In 2015, Phillippe was cast in the lead role of Bob Lee Swagger on the USA Network thriller drama series Shooter, which premiered in November 2016.

[55] In February 2020, Phillippe was announced in the role of Cody Hoyt in the ABC crime drama series Big Sky, which was created by David E.

Phillippe and Witherspoon, who was six months pregnant, married on June 5, 1999, in a small ceremony at the Old Wide Awake Plantation near Charleston, South Carolina.

[73] In September 2017, Elsie Hewitt, an ex-girlfriend of Phillippe, filed a lawsuit against him for allegedly punching her, kicking her, and throwing her down stairs.