2000 was a solid year for Michael Douglas: His starring role as American drug czar Robert Wakefield in Steven Soderbergh’s critical and commercial darling Traffic was widely praised. The same goes for Frances McDormand: She received a Best Supporting Actress Academy Award nomination for her turn as strict mother Elaine Miller in Cameron Crowe’s beloved Almost Famous. Robert Downey Jr.’s career was careening up and down as a result of his drug addiction and run-ins with the law, but his supporting role on Ally McBeal was one step in a long comeback. Pre-Spider-Man Tobey Maguire was getting attention for his work in period pieces like The Cider House Rules and Ride with the Devil; Katie Holmes was expanding her Dawson’s Creek fame and transitioning into more film work. And if you forgot they were all in the endearingly quirky, surprisingly sentimental Wonder Boys together, well, you can’t be blamed for that. A commercial failure that didn’t secure a contemporary audience, Wonder Boys’s farcical absurdity (and some of its approaches to gender and race) have noticeably aged. But the complicated relationship it captures between creativity and self-worth, and the grace it extends to its uniformly messy characters, are as fresh as ever. (Soderbergh knows this; his latest, Let Them All Talk, examines the same broad themes.)
Paramount Pictures tried its hardest to make Wonder Boys a success. Everything seemed right: L.A. Confidential Academy Award winner Curtis Hanson was directing an adaptation of acclaimed novelist Michael Chabon’s same-named novel. Established stars Douglas and McDormand were sharing the screen with reformed bad boy Downey and up-and-comers Maguire and Holmes. The soundtrack was a veritable classic-rock orgy of Bob Dylan, Van Morrison, Neil Young, Leonard Cohen, and John Lennon. After the film bombed at the box office with a February 2000 release date, Paramount re-released it in November in a move Entertainment Weekly called “nearly unheard of”: “Paramount’s abiding faith in the film … prompted them to admit to and revise marketing mistakes, including a new ad campaign (potential cost: $10 million) and the release date it should have had in the first place.”
Admirable! But not fully successful: While Wonder Boys (streaming on Amazon Prime and Hulu as of Jan. 1) garnered a few Academy Award nominations (Best Adapted Screenplay and Best Film Editing, and Bob Dylan won a Best Original Song award for the film’s opening track “Things Have Changed”) and ended up on various critics’ best-of lists, it never made back its $55 million budget. As film critic Sean Burns notes, “It’s somehow fitting that Wonder Boys managed to flop twice, as the movie is practically a valentine to failure — a warmly humane and often side-splittingly funny exploration of underperforming against expectations.”
Douglas remained a champion of the film—hosting a 2018 screening of it at Massachusetts’s legendary Coolidge Corner Theatre, during which he praised the film’s “great writing” by Steve Kloves—and when Hanson passed in 2016, many obituaries, including Stephen Dalton’s at The Hollywood Reporter, said the film “proved Hanson was no one-hit wonder boy himself.”
That exuberantly supported but widely underseen vibe fits Wonder Boys, a film that explores the strange events of one weekend at an unnamed Pittsburgh university and that asks whether we’ll recognize our own downswing while we’re in it. Would we see the mistakes we’re making, or the lies we’re being told, or the role we’re serving in someone else’s story, while those things are happening? Or are we unable to break out of a certain cycle and deviate from a certain path? “Couldn’t stop,” literature professor Grady Tripp (Douglas) says when someone asks of his 2,611-page, still-unfinished novel, “Why were you writing?” But every story has a beginning, and every story has an end.
Wonder Boys begins during a writing workshop, the kind of round-robin-style format any creative writing or humanities graduate student will recognize: the sense of laying yourself bare by sharing your work, the courage it takes to receive feedback with which you might not agree, and the acknowledgement that what you wrote might, in fact, need editing, improvement, or reassessment. So many of the details of Hanson’s world-building, Kloves’s script, and Jeannine Oppewall’s production design make real the utterly unique rhythms of campus life, the fluid boundaries between professors and students, and the idea of college as a place of reinvention. The casualness with which students like Hannah (Holmes) and James (Maguire) address Professor Tripp, with their knowledge of the details of his marriage, the status of his incomplete novel after the resounding success of his preceding work, The Arsonist’s Daughter, his constant marijuana smoking, and his push-pull relationship with his editor, Terry Crabtree (Downey). Tripp’s openness with them about his wife having recently left him, the demands of finishing his book, and the inadequacy he feels compared with other authors who arrive on campus for the university’s annual Wordfest event. The intimacy with which they all share space—Hannah rents a room in Tripp’s house; James is always hanging around—and the sense that in their shared artistic ambition, they’re all equals, too. (Cinematographer Dante Spinotti’s recurring use of split diopter shots that equate Tripp and James and James and Hannah within the frame adds to that atmosphere.)
But the nature of a college campus is that one, usually younger, generation arrives, moves through it, and then leaves it behind, while another, usually older, cadre of professors and administrators stays still, and that dichotomy has manifested in Tripp as a kind of listlessness.
Wonder Boys gives you the sense that Tripp hasn’t made a true decision of his own in a long time, and that for all the guidance he offers his students, for all the indulgence he provides to James’s increasingly complex and contradictory stories about his childhood, and for all the kindness with which he rebuffs Hannah’s advances, he’s just floating along. He goes to Wordfest every year and stands by as his boss, the head of the English department, Walter Gaskell (Richard Thomas), praises visiting author after visiting author. He puts on his ratty pink robe, sits at his typewriter, and types away some before locking his meandering pages in a file cabinet. He arranges secret rendezvous with Sara Gaskell (McDormand), the university chancellor and Walter’s wife, with whom he’s been having an affair. He is constantly smoking a joint, pulling one out of his pocket or fetching one from the glove compartment of his car—the weed as ubiquitous as the red cowboy boots Hannah always wears, or the many overdue library books and VHS movies in James’s knapsack, or the unending line of men and women Terry sleeps with and then casts aside.
Tripp has become a predictable man. But when Sara tells him that she’s pregnant, he’s finally jarred out of the holding pattern that becomes his life, setting off an unpredictably peculiar series of events. In the 25 years that have passed since Chabon’s novel was published, and the 20 years since Wonder Boys was released, our reactions to some of these subplots might have changed (how Tripp glibly calls Terry’s latest paramour a “transvestite”; how Hannah is a sort of literary manic pixie dream girl who thinks Tripp and James are both geniuses and provides them with alternating encouragement and tough love; how Terry, Tripp, and James giggle over a backstory they imagine for a Black man they see at a bar). And although McDormand is her usually excellent no-nonsense self, contrasting well with Douglas’s potheaded bemusement, Wonder Boys is very much a movie about, well, boys: the promising writer Tripp once was, the promising writer James now is, and Terry’s role in both their careers.
The three of them are mostly in orbit around each other, doing a complicated dance of ambition, resentment, and opportunity. Downey’s Terry is the most interesting character onscreen in any scene he’s in, a man looking for his next big discovery, all smooth talk and amused energy. Maguire is a wide-eyed lamb as the incredibly sensitive wunderkind James, who can rattle off movie character suicides, is moved to tears thinking of Marilyn Monroe’s fame and loneliness, and is a phenomenally compelling liar. And Douglas, bedecked in a pair of tortoiseshell glasses, ratty beanie, and overly long scarf that are meant to foreground him as a “kooky English professor” archetype, makes clear that Tripp is a man slowly trying to be honest to himself and to others, but unsure of what it takes to get there. He lingers a little too long reading James’s secret novel, watching Sara in her greenhouse, and sitting in his soon-to-be-ex-wife’s family home, revealing to her father how little he really knew about the daughter that he married. As those scenes stretch out, Douglas holds your attention as an uncertain man going with the flow of odd situations—a practically nonsensical conversation with James’s parents, a tête-à-tête with the Black man from the bar—as he wonders whether anything he’s done has mattered. “Books, they don’t mean anything. Not to anybody. Not anymore,” Tripp says, but of course he’s wrong about that, and Wonder Boys is passionate in its defense of storytelling as one of the last remaining methods of truth telling in our world.
That insistence that the written word matters, and that it unifies us in ways you wouldn’t anticipate, suffuses Wonder Boys with the kind of warm sincerity that defined films like Almost Famous and Pump Up the Volume, too: films that found their characters desperately searching for some kind of purpose in a world that seems uncaring, unfriendly, and uncomfortable. That can seem like an impossible struggle, but Wonder Boys posits the creation of art as a kind of escape, and the bond you form with others striving toward the same thing as a sort of rescue. “We need all the downy innocents we can get,” Tripp tells Hannah, and the environment of heartfelt affection and light mockery in which Wonder Boys situates its characters is worth revisiting.