Winona Ryder in Mojo Nixon: Debbie Gibson is Pregnant with My Two-Headed Love Child (1989)

Winona Ryder, Shannen Doherty, Lisanne Falk, and Kim Walker in Heathers (1988)

Winona Ryder and Justin Theroux in Beetlejuice Beetlejuice (2024)

Winona Ryder and Michael Keaton in Beetlejuice Beetlejuice (2024)

Winona Ryder, Catherine O'Hara, Justin Theroux, and Jenna Ortega in Beetlejuice Beetlejuice (2024)

Winona Ryder in Bram Stoker's Dracula (1992)

Gary Oldman and Winona Ryder in Bram Stoker's Dracula (1992)

Johnny Depp and Winona Ryder in Edward Scissorhands (1990)

Winona Ryder, Shannen Doherty, Lisanne Falk, Kim Walker, and Heather Abbott in Heathers (1988)

Winona Ryder and Michael Lehmann in Heathers (1988)

Winona Ryder and Christian Slater in Heathers (1988)

Michelle Pfeiffer, Winona Ryder, and Daniel Day-Lewis in The Age of Innocence (1993)

Kenneth Branagh, Leonardo DiCaprio, Winona Ryder, Charlize Theron, Melanie Griffith, Famke Janssen, Judy Davis, Joe Mantegna, and Bebe Neuwirth in Celebrity (1998)

Drew Barrymore, Winona Ryder, Adam Sandler, and John Turturro in Mr. Deeds (2002)

Winona Ryder and Gena Rowlands in Night on Earth (1991)

Winona Ryder, Roberto Benigni, Béatrice Dalle, and Isaach De Bankolé in Night on Earth (1991)

Winona Ryder in Welcome Home, Roxy Carmichael (1990)