Over the years Winger acquired a reputation for being outspoken and sometimes difficult to work with. Their son Gideon Babe Ruth Howard (known as Babe) was born in 1997. She is stepmother to Sam Howard.
She has also been nominated for four Golden Globe awards two BAFTA awards an Emmy Award and won the National Society of Film Critics Award for Best Actress for Terms of Endearment and the Tokyo International Film Festival Award for Best Actress for A Dangerous Woman. She then gave Academy Award-nominated performances in An Officer and a Gentleman Terms of Endearment and Shadowlands.