She starred in the films An Officer and a Gentleman (1982), Terms of Endearment (1983), and Shadowlands (1993), each of which earned her a nomination for the Academy Award for Best Actress.

Winger's other films include Urban Cowboy (1980), Legal Eagles (1986), Black Widow (1987), Betrayed (1988), The Sheltering Sky (1990), Forget Paris (1995), and Rachel Getting Married (2008).

She received a lifetime achievement award at the Transilvania International Film Festival in 2014,[3] and starred in the Netflix original television series The Ranch (2016–2020).

[7] At age 18, after returning to the U.S., she was involved in a car crash and suffered a cerebral hemorrhage; as a result, she was left partially paralyzed and blind for 10 months, initially being told that she would never see again.

Her next role was as Diana Prince's younger sister Drusilla (Wonder Girl) in three episodes of ABC's TV series Wonder Woman.

In 1982 she co-starred with Nick Nolte in Cannery Row and with Richard Gere in An Officer and a Gentleman, for which she was nominated for the Academy Award for Best Actress.

[14] Other starring roles during this period included Legal Eagles, Made in Heaven, Everybody Wins, The Sheltering Sky, Leap of Faith, Black Widow, Betrayed, Wilder Napalm, and A Dangerous Woman.

[15] After making Forget Paris in 1995, she was absent from the screen for six years before returning in 2001 with Big Bad Love, written and directed by her husband, Arliss Howard.

[16] During her film hiatus, Winger had the female lead in the American Repertory Theater's stage production of Anton Chekhov's play Ivanov from November 1999 to January 2000.

Winger subsequently starred in the films Radio, Eulogy, and Sometimes in April, and received positive reviews for portraying Anne Hathaway's estranged mother in Rachel Getting Married.

[18] Winger earned an Emmy Award nomination for her title role as the mother of a Columbine shooting victim in the 2005 television film Dawn Anna, directed by Arliss Howard.

[20] In 2013, Winger starred in three episodes of In the Woods,[21] the first installment of Jennifer Elster's multimedia, experimental film series The Being Experience, also including Terrence Howard, Dave Matthews, Rufus Wainwright, Karen Black, Will Shortz, Liya Kebede, Questlove, Famke Janssen, Moby, Gale Harold, Paz de la Huerta, Jorgen Leth, Rosie Perez, Aubrey de Grey, and Alan Cumming.

[22] From 2016 to 2020, Winger starred opposite Sam Elliott and Ashton Kutcher in the Netflix multi-cam comedy The Ranch.