Jami Gertz. Around 1984, when they met on Sixteen Candles.
Claire Forlani She’s also a former Brad Pitt girlfriend, and current wife of Dougray Scott.
Janice Dickinson. She had sex with Cusack on a plane, said he had a huge dick, and also that he’s humorless. Also note, I kept putting in searches for “Young Janice Dickinson, and Google kept returning what I thought were images of young Phoebe Cates.
Melissa Gilbert. She actually cheated on her then fiance, Rob Lowe, with John Cusack, after she found out that Rob Lowe was sleeping with Nastassja Kinski.
Lili Taylor. Apparently, Cusack also dated his Say Anything co-star, although she also dated Cusack’s friend, D.V. DeVincentis.
Gina Gershon. She’s also dated Owen Wilson and … Beck.
Susannah Melvoin. The singer best known for her association with Prince lived with John Cusack circa Bullets Over Broadway.
Minnie Driver. The two met on Grosse Point Blank. Driver has also dated Harrison Ford and Matt Damon.
Alison Eastwood — The two met on the set of Midnight at the Garden of Good and Evil, directed by Clint Eastwood.
Neve Campbell. Cusack and Campbell were together long enough that there were rumors that they were engaged, although if this Blind Item is to be believed, Cusack was not a very good boyfriend.
Jodi Lyn O’Keefe — Cusack had apparently dated her for years in the 2000s, and there were even some specious reports that they’d been secretly married. They broke up, according to rumors, because Cusack wouldn’t commit to marriage.
Jennifer Love Hewitt. The two had a fling back in 2003.
Alexandra Kerry. He briefly dated the daughter of Secretary of State John Kerry back in 2004.
Brooke Burns — Cusack dated the former Baywatch star in 2010.
Uma Thurman — Cusack and Thurman dated after she divorced Gary Oldman, and were seen together again after she split with Ethan Hawke.