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For the last few years of the ’80s and the bulk of the ’90s, there was no young Hollywood actress who was as compelling as Winona Ryder. Picking up two Oscar nominations for her roles, providing pitch-perfect voice-over narration for the majority of her films, and serving as an aspirational fashion icon (and one who carried a brainy depth to boot), Ryder was a high-ranking member of Hollywood’s A-list. While her work in the new millennium has not been as strong as her string of hits in the ’80s and ’90s (such is the career trajectory for many a young woman working in the film industry), you can’t deny her extremely brilliant — and surprisingly diverse — roles toward the end of the last century.

'Beetlejuice' (1988)

Though she’d had small roles in a few movies in the mid- to late-’80s, Ryder’s breakthrough role is inarguably as Lydia Deetz in Tim Burton’s horror comedy. As the sullen goth girl who’s whisked from Manhattan to the country by her manic and quirky parents, Lydia finds comfort in the fact that she has the ability to see and befriend the two ghosts who are haunting her parents’ new house — that is until they summon the titular “bio-exorcist” to wreak havoc on the Deetzes. [Where to stream Beetlejuice]

'Heathers' (1989)

In this pitch-black comedy that served as a spiritual end to the rush of teen movies produced in the ’80s, Ryder plays an unexpected popular girl whose three best friends (all named Heather) rule their high school’s caste system. But when she meets a mysterious and brooding new student played by Christian Slater, they upend the social status quo by killing off the cruelest (and most popular) kids in school. [Where to stream Heathers]

'Mermaids' (1990)

Most people rebel against their parents. When your mother is a glamorous and flighty gal played by Cher, it’s only natural to go running in a pious and true direction. Ryder plays a teenage rebel (who rebels through Catholicism) in this classic, ’60s-set coming-of-age story, which also features Christina Ricci in her first role. [Where to stream Mermaids]

'Edward Scissorhands' (1990)

Donning a blonde wig, Ryder transformed herself from the awkward, brainy girl into the gorgeous, romantic ideal in Tim Burton’s fantasy romance, playing the love interest to (her then off-screen boyfriend) Johnny Depp’s titular robotic man child. [Where to stream Edward Scissorhands]

'Bram Stoker's Dracula' (1992)

Ryder went full sexpot in Francis Ford Coppola’s bloody and sensuous retelling of the classic vampire story. Playing Mina Harker, Ryder is fully seduced by Gary Oldman’s Count Dracula, and in turn transforms into a ravenous woman desperate for the love of an ancient undead being. [Where to stream Bram Stoker’s Dracula]

'The Age of Innocence' (1993)

Ryder earned her first Oscar nomination as the seemingly innocent May Welland, the young bride-to-be to Daniel Day-Lewis’ Newland Archer. But when Archer begins an affair with the scandal-ridden Ellen Olenska (Michelle Pfeiffer), Welland’s naive façade fades away in favor of her upper-crust-society-induced conspiratorial nature. [Where to stream The Age of Innocence]

'Reality Bites' (1994)

In Ben Stiller’s quintessential Gen-X romantic comedy, Ryder plays eager post-grad Lelaina Pierce, who, after losing her entry-level job as a production assistant on a morning talk show, quickly learns the world is not her oyster. Additionally, she’s caught in one of the most frustrating love triangles in modern cinema history. [Where to stream Reality Bites]

'Little Women' (1994)

Ryder earned her second Oscar nomination (this time for Best Actress) in this beloved adaptation of Louisa May Alcott’s classic novel, playing the plucky and ambitious Jo March. Ryder shares the screen alongside Susan Sarandon, Christian Bale, Claire Danes, Kirsten Dunst, and Gabriel Byrne. [Where to stream Little Women]

'The Crucible' (1996)

Reteaming with Daniel Day-Lewis, Ryder takes her shot at playing the villain for once as Abigail Williams, the mastermind behind the Salem Witch Trial accusers who attempts to cover up her sordid personal history by pointing the finger at many of her fellow Puritan neighbors in this adaptation of Arthur Miller’s classic play. [Where to stream The Crucible]

'Girl, Interrupted' (1999)

Although she’s a bit overshadowed by Angelina Jolie’s manic, Oscar-winning performance, Ryder is perfect as Susanna Kaysen in this adaptation of the author’s memoir of her time at a mental institution in the late ’60s — a passion project that she also executive produced. [Where to stream Girl, Interrupted]

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