Upon the publication of the coming-of-age novel The Mysteries of Pittsburgh in 1988, Michael Chabon earned recognition as a promising young fiction writer. The story centers on Art Bechstein, who has recently graduated from college and is about to experience what he perceives as the last summer of his youth. Shortly into that summer, Art befriends a witty homosexual, Arthur, and two appealing women. He becomes the lover of one of the women, Phlox. The other woman is the lover of Arthur's best friend, the opportunist Cleveland. When Cleveland learns that Art's father is a racketeer, he pressures Art into making introductions. Art cooperates, but it costs him his father's remaining respect. Frustrated by that paternal disdain, Art falls into an emotionally confusing, but nonetheless fulfilling, affair with Arthur. Cleveland, who has profited from the patronage of Art's father, then reappears with stolen goods. He is fleeing both the law and the mob--that is, Art's father. Violence ensues, and Art and Arthur are compelled to run for their lives.

The Mysteries of Pittsburgh won Chabon recognition as a gifted new storyteller. "Here," proclaimed Alice McDermott in the New York Times Book Review, "is a first novel by a talented young writer." Chabon, McDermott declared, "skillfully sets down the elements of his plot [and] diligently sets them spinning." She added that "his control over his story, the wonderful use he makes of each description, of Pittsburgh itself, are often astonishing." Another enthusiast, Brett Lott, wrote in the Los Angeles Times Book Review that The Mysteries of Pittsburgh constituted a "remarkable" achievement, and he lauded the novel for its "heart, [its] compassion for characters simply trying to wade through a world too filled with itself to let real love surface, breathe, and take us in." And New Statesman reviewer M. George Stevenson, who was not alone in likening Chabon to author F. Scott Fitzgerald, noted: "Making a reader experience again a sense of endless possibility is one of the most satisfying and quintessentiall American things an American bildungsroman can do. Chabon's The Mysteries of Pittsburgh adds to the canon one of the rare novels actually able to do it."

Chabon followed The Mysteries of Pittsburgh with A Model World, and Other Stories, which includes tales he had already published in New Yorker. Many of the stories here involve unrequited love, and five of the tales--collectively termed "The Lost World"--chart the angst of adolescent Nathan Shapiro as he grows from age ten to sixteen. Among these chronicles is "The Little Knife," where he agonizes over both his parents' antagonistic relationship and the Washington Senators' imminent demise from major-league baseball. In "More Than Human," a tale focusing on Shapiro, he must come to terms with his shattered family after his father leaves home. Another story in A Model World, "Blumenthal on the Air," centers on an American narrator who marries an Iranian woman simply to provide her with United States citizenship. He then finds himself falling in love with her.

In her New York Times Book Review appraisal of A Model World, Elizabeth Benedict complained that Chabon sometimes uses his polished style as a means of remaining emotionally aloof from his material. "All too often he keeps his distance," she alleged. But she added that even in tales where Chabon remains reserved, he nonetheless manages to produce "fluent, astonishingly vivid prose." Benedict was particularly impressed with "The Lost World" group, which she lauded for its "breathtaking" descriptive passages. Other tales in the volume, Benedict noted, recalled The Mysteries of Pittsburgh. Such stories, she affirmed, "have a kaleidoscopic beauty."

Chabon experienced considerable difficulty in trying to follow up the success of The Mysteries of Pittsburgh and A Model World. While living on a large advance from his publisher, he wrote 1,500 pages of what he intended to be his second novel, Fountain City. It was, Chabon told Los Angeles Times contributor Erik Himmelsbach, "sort of a map of my brain," and in it, he attempted to express his love for Paris, architecture, baseball, Florida, and more. After four and a half years and four drafts, however, Chabon admitted to himself that he was never going to be able to craft Fountain City into a readable book. He explained to Himmelsbach, "Because I had taken that [advance] money, I felt like I couldn't dump the project, even when it was fairly clear to me that it wasn't working."

The Fountain City experience was demoralizing, but Chabon eventually turned it to his advantage. In early 1993, he began work on Wonder Boys, and in less than a year he had finished his second novel. Wonder Boys is a fast-paced, comic romp that chronicles one long, disastrous weekend in the life of Grady Tripp, a once-lauded writer now burdened with a 2,000-page manuscript he cannot finish. Joseph P. Kahn of the Boston Globe called Tripp "an instant classic . . . part Ginger Man, part Garp and altogether brilliantly original." The plot includes "an itchy editor, a pregnant mistress, a befuddled protege, a pilfered tuba, [and] a dead dog," noted Kahn. Chabon confided to Lisa See in Publishers Weekly that until his wife read the manuscript of Wonder Boys and he heard her laughing as she turned the pages, he had no idea that he was writing a comic novel. "To me, Grady has a wry tone, but I felt sad writing about him. In a lot of ways, he is a projection of my worst fears of what I was going to become if I kept working on Fountain City." He continued: "To me, the book is about the disappointment of getting older and growing up and not measuring up to what you thought, and the world and the people in it not being what you expected. It's about disillusionment and acceptance."

Wonder Boys was hailed as a worthy successor to The Mysteries of Pittsburgh and A Model World by many critics. "Despite (or maybe because of) his failings, Grady Tripp is an appealing hero," affirmed Robert Ward in the New York Times Book Review. "We feel for him as he struggles with his behemoth of a novel, as he broods about love and literature. . . . He's very much a lovable mess." Ward found that "stylistically, Mr. Chabon is, as always, a pleasure to read. `Wonder Boys' is filled with memorable lines and wonderful images. . . . Chabon is that rare thing, an intelligent lyrical writer. Because his comedy always reins in his romantic impulses, his work seems to reflect a nature that is at once passionate and satirical. The result is a tone of graceful melancholy punctuated by a gentle and humane good humor."

Some reviewers were less enthusiastic, however. Time's John Skow remarked that Wonder Boys is "a series of funny scenes about not writing a novel that somehow don't hang together as a novel." Yet others, such as Roz Kaveney, differed sharply in their assessment of Chabon's achievement. Kaveney wrote in a New Statesman & Society review that Wonder Boys "is a virtuoso performance with a sequence of comprehensively visualised backdrops and enough well-rounded walk-ons to people a novel twice its length. . . . This is a great book about personal disaster."

Although he has often been grouped with other writers of his generation such as Bret Easton Ellis and Jay McInerney, many critics feel Chabon's work bears no resemblance to their flat, enervated narratives of disaffected youth. "Unlike other authors of his age, Chabon embraced, rather than scorned, the power of words and language; his writing was lively, funny, involving, beautiful, the kind of stuff from which great literature is made," declared Himmelsbach. He quoted Chabon as saying: "I just want to write things that last. . . . My first intention has not been to reflect the time in which they were written. I'm not trying to get the '90s or the '80s or whatever down on paper in America at all. I'm just trying to write the best English I can write."