Writing isn’t a horse race, they tell you when you’re starting out. And it’s true, or at least it should be true, for if you spent all your time comparing yourself to other writers, you’d be trapped in an endless cycle of gloating and ritual seppuku. But sometimes the trajectories of certain writers’ careers are so surprising that you can’t help but compare them to their contemporaries and think: what happened? Why does one writer wind up with a massive readership, another in obscurity, and a third in some special “writer’s writer” place? Such is the case with Philip Roth and Bruce Jay Friedman, two writers I have often read and loved over the years.

Friedman and Roth in the 1960s

These days, their profiles are so different, and overall, their respective bodies of work have little in common. But once, long ago, they could have been brothers. Both brainy, self-effacing, brutally funny, together they were part of the literary arm of a Freudian-inflected comedic fraternity in 1960s America. While the seemingly extemporaneous riffs of the actual stand-up comedians in that bunch were, of course, actually written (and rewritten), the effect was pure spontaneity: nebbishy hipsters sitting around at a party, smoking and remembering.

This was not the case with either Friedman or Roth. Their early work owed a great deal to “remembrance,” as most fiction does, but not a word felt casual or carelessly chosen, and the comedy contained within was always in the service of character and story. In an interview, Roth once named Bellow and Malamud as influences, rather than more comedic writers. Still, the high comedy of Portnoy’s Complaint is unarguable. Published in 1967, the novel begins, famously, with Alexander Portnoy’s mother:

She was so deeply embedded in my consciousness that for the first year of school I seem to have believed that each of my teachers was my mother in disguise. As soon as the last bell had sounded, I would rush off for home, wondering as I ran if I could possibly make it to our apartment before she had succeeded in transforming herself.

The prose is stylistically different from mentor Bellow’s often genuinely funny but stately tone. It’s a lot less different from Bruce Jay Friedman, however, whose second novel, the classic A Mother’s Kisses, appeared in 1964, three years before Portnoy:

Once, when he was five, a Negro woman had been assigned to watch him through the summer, allowing him to wander only twenty paces in each direction. Each time he reached the edge of a building and tried to go around it she would rein him back to the side. He spent the summer a lidless city pavement animal, tied to a chain, wheeling drugged and lazy in the sun. Now, twelve years later, it seemed to Joseph that he was chained again and that there was nothing to do but stand in front of his apartment house and stretch and try to breathe and wait for the days to pass.

The novel, in the hands of these two men, becomes a comic catalogue of torture and longing. Willing and eager to use themselves as the brunt of jokes, their early characters find themselves in frustrated and servile positions beside overwhelming women of all kinds. But the anger toward women in their novels feels partly analyzed, a far cry from the indignant posturing of an über-male writer like Norman Mailer and even, to some extent, Bellow himself, whose misogyny sometimes feels so raw it can be feral. Does the power of Friedman’s and Roth’s early work lie principally in the fact that they were willing, at times, to depict men as unreconstructed bewildered shmucks or shlemiels in a way that few other writers did? In throwing vanity aside in these formative novels, they occasionally achieved a state that resembles the psychoanalytic ideal: self-reflection unsullied by defensiveness.

But the story of these two writers, like all good stories, has its twists. Bruce Jay Friedman continued publishing novels and short stories, as well as writing the play Steambath, which was produced off-Broadway and for PBS. In Hollywood, he wrote screenplays for Doctor Detroit and Splash. Friedman’s humor book, The Lonely Guy’s Guide to Life was turned into a Steve Martin movie, and one of his short stories became the classic Elaine May film The Heartbreak Kid. Friedman chronicled Hollywood directly in his novel About Harry Towns, in which the eponymous protagonist’s life as a screenwriter and bicoastal, divorced father is mined for both dark comedy and melancholy. The book instills in me undiluted wistfulness for an era—the 1970’s—when fiction could be “character-based” and still feel big and exciting. Friedman has always been an essentially modest writer, which is a part of his charm. Few postmodern tricks have graced his pages. His characters are plaintively themselves, and the story lines are simple. The comedy is innate, sad, and human.

Roth, along the way, became bigger and bolder and, in a sense, trickier. His fictional alter-ego Nathan Zuckerman appeared in his work regularly, and the self-referential nature of the Zuckerman novels helped to increase the myth of Roth himself. Bruce Jay Friedman carried no whiff of myth, and his body of work is not, like Roth’s, ready-made for scholar-detectives. These two writers, who started out in a similar vein, have had entirely divergent trajectories, and the causes of this are complicated, though Roth’s incredible output surely has had something to do with it. Through his fecundity and also, recently, through work that draws from the political culture, he has remained relevant and has refused to go gently into that remainder bin, where so many writers of his age have been sent. And then there’s Bruce Jay Friedman’s Hollywood connection, which has probably sullied his reputation in the eyes of literary purists, who think that fiction writers who also do screenplays are by nature sellouts (as opposed to being writers who would like to feed and clothe their families). But ultimately it’s the actual nature of Friedman’s fiction that has affected his standing—at least in comparison to someone like Roth’s. Over the years, Friedman has stayed “funny,” while Roth, mostly, has not.

In the 1960s and 70s, humor was an inextricable part of being “literary;” this was a time when Vonnegut and Heller and others were writing freely and wildly. But nowadays America likes its literary writers to be somber and poker-faced. And those writers, in certain instances, have obeyed, as if understanding that fun and games are for the young, and that time is rapidly passing and reputations are at stake. Philip Roth has always followed his obsessions, which took him on a literary crashcourse from the high hilarity of perpetual masturbation to the pain and fear of death. Bruce Jay Friedman hasn’t taken such a direct and furious path, but instead, over all the last three decades, has continued to explore the big and small human themes in his own way, as though he’s got all the time in the world.

And now, upon entering what will perhaps be the final big phases of fecundity in their writing lives, there’s a way in which both writers’ work has ended up, if not in the same place, at least in parallel places. Roth’s most recent novel, Everyman, contains easily recognizable Rothian stuff: the intense early memories, including an achingly wistful set-piece about a surgery the protagonist endured as a child, and then some “Have you learned NOTHING?” anecdotes about his relationships with the women in his life. The whole book ends, of course, in death, which hangs over this book the way the phallus once hung over Portnoy’s Complaint.

Friedman’s new book, just published, is a very different entity. Sexual Pensées isn’t fiction at all, and is essentially a confection, consisting of little anecdotes and pastiches about Friedman (or some stylized version of him) having sex and thinking about having had sex. Some of the tiny haiku and koan-like reminiscences are on the order of Woody Allen: “It annoyed him that he had lost a woman he cared about to a herring czar.” Others bear a certain philosophical acceptance: “With the help of Viagra, he returned to sexual form, so to speak, at age seventy. Oddly enough, he had mixed feelings about this sudden renewal.” The book is illustrated with drawings that look a little bit like outtakes from the original The Joy of Sex, and the whole thing is infused with a sweetness and a distinct lack of young-man’s urgency.

Different as these books may be—one somber; the other light—they ultimately point to the similar preoccupations of two masterful writers. The truth, of course, in both Everyman and Pensées and, of course, in life itself, is that death trumps sex every time