Ethan Hawke

1985–1993: Early years and breakthrough

With his mother's permission, Hawke attended his first casting call at age 14 and was cast in Joe Dante's Explorers (1985), playing a misfit schoolboy alongside River Phoenix. The film received mixed reviews and performed poorly at the box office, leading Hawke to step away from acting for a time. He later described the experience as difficult to handle at such a young age, remarking, "I would never recommend that a kid act". In 1989, Hawke had his breakthrough role as a shy boarding school student in Peter Weir's Dead Poets Society. The film was critically and commercially successful and won the BAFTA Award for Best Film. Reflecting on the impact of its success, Hawke later said, "I didn't want to be an actor and I went back to college. But then the film's success was so monumental that I was getting offers to be in such interesting movies and be in such interesting places and it seemed silly to pursue anything else." After filming Dead Poets Society, he auditioned for his next project, the comedy-drama Dad (1989), and settled in New York City due to its prominent theater industry and variety of opportunities.

In 1991, Hawke co-founded Malaparte, a Manhattan-based theater company that operated until 2000. His first leading role came with Randal Kleiser's film White Fang (1991), an adaptation of Jack London's novel of the same name, in which he portrayed a young Klondike gold prospector who befriends a wolfdog. A writer for The Oregonian appreciated how he kept the film from "being ridiculous or overly sentimental", while Roger Ebert praised how he was "properly callow at the beginning and properly matured at the end"; Hawke himself later called it the "single best experience of my acting life". In A Midnight Clear (1992), his character leads a group of American soldiers during World War II, tasked with capturing a small squad of German troops stationed in the Ardennes forest in France. Hawke made his Broadway debut in 1992, portraying the playwright Konstantin Treplev in Anton Chekhov's The Seagull at the Lyceum Theater in Manhattan. He then played Nando Parrado, one of the survivors of the Uruguayan Air Force Flight 571 crash in the Andes, in the survival drama Alive (1993), adapted from Piers Paul Read's 1974 non-fiction book.

1994–2000: Established leading man

In 1993, actress Winona Ryder offered Hawke a leading role in Ben Stiller's Generation X drama Reality Bites (1994). Hawke was reluctant to accept the offer due to his dislike of the characters, but he reconsidered it because he admired Ryder and appreciated the script. The film grossed $41 million on a budget of $11 million and later became a cult classic; of Hawke's performance, Owen Gleiberman said he had "suddenly grown up into a magnetic performer". With Reality Bites, Hawke attained celebrity status and became known as an alternative heartthrob, a perception fueled by his blue eyes, well-defined jaw, goatee, and tousled hair. His portrayal of a disillusioned musician in the film led to him being strongly associated with the character and deemed the poster boy of Generation X, with journalist Vanessa Grigoriadis describing his image at the time as "the sensitive pretty boy hanging around a patchouli-scented dorm hall discussing the meaning of life". Hawke felt initially irked by the label, believing it to be a restricting marketing term, but he embraced it later in his career.

Instead of accepting roles in big-budget Hollywood films offered to him, Hawke chose to collaborate with directors whom he believed "could stoke his creativity", starring in Richard Linklater's Before Sunrise (1995) among others. Linklater said that, at the time, he had been searching for actors as well as creative partners, inviting Hawke and co-star Julie Delpy to contribute to the dialogue and character development with their own personal experiences. The first installment of the Before film trilogy, Before Sunrise follows an American man (Hawke) and a French woman (Delpy) who meet on a train and disembark together in Vienna. The film received positive reviews praising Hawke and Delpy's performances; The Hollywood Reporter retrospectively called it "one of cinema's most sustained explorations of love and the passage of time".

Hawke directed the music video for Lisa Loeb's US Billboard Hot 100 number-one single "Stay (I Missed You)"; Loeb was then a member of Hawke's theater company. Spin magazine named the video its Video of the Year in 1994. Hawke appeared in a 1995 production of Sam Shepard's Buried Child, directed by Gary Sinise at the Steppenwolf Theater in Chicago. In 1996 he published his first novel, titled The Hottest State, which tells the story of a love affair between a young actor and a singer. He described writing the book as both the "scariest  [... but also] one of the best things I ever did." Entertainment Weekly said Hawke "opens himself to rough literary scrutiny in The Hottest State. If Hawke is serious [...] he'd do well to work awhile in less exposed venues." The New York Times thought Hawke did "a fine job of showing what it's like to be young and full of confusion", concluding The Hottest State was ultimately "a sweet love story".

Hawke called his script in Andrew Niccol's science fiction film Gattaca (1997) "one of the more interesting" ones he had read in "a number of years". In it, he played the role of a man who infiltrates a society of genetically perfect humans by assuming another man's identity. Ebert called him a good choice for the lead role, stating that he "combin[es] the restless dreams of a 'Godchild' with the plausible exterior of a lab baby". Alongside Gwyneth Paltrow and Robert De Niro, he starred as a modern-day Pip in Great Expectations (1998), a contemporary film adaptation of Charles Dickens's 1861 novel of the same name, directed by Alfonso Cuarón. Hawke criticized the film's time of release, stating that "nobody gave a shit about anything but Titanic for about nine months after [...] particularly another romance". He collaborated with Linklater once again on The Newton Boys (1998), based on the true story of the Newton Gang. The film saw generally negative reception; Rotten Tomatoes' consensus said the "sharp" cast made up for "the frustrations of a story puzzlingly short on dramatic tension".

In 1999, he starred as Kilroy in the Tennessee Williams play Camino Real at the Williamstown Theater Festival in Massachusetts. That year, Hawke starred in Snow Falling on Cedars, adapted from David Guterson's novel of the same name. Set in the 1950s, he played a young reporter who covers the murder trial of a fisherman. The film received a tepid response, with Entertainment Weekly commenting that "Hawke scrunches himself into such a dark knot that we have no idea who [his character] Ishmael is or why he acts as he does". Hawke's next film role was in Michael Almereyda's Hamlet (2000), in which he played the titular character. The adaptation set William Shakespeare's play in contemporary New York City, a choice Hawke said made the story feel more "accessible and vital".