Writers’ friendships are often tricky, fraught with twinges of rivalrous competition and subject to tidal ebbs and flows of esteem. It’s rare, for example, to see the otherwise touchy Henry James subside into universal admiration, as he did for Ivan Turgenev in his 1888 essay “I.T.,” but of course that was a eulogy, and so the latent battle was over . . . Besides, Turgenev was a rich gentleman of the old Russian school , and James didn’t have to put up with him as much as he did Edith Wharton, whose sometimes unwelcome visits he described as “the Angel of Devastation” descending on his country place in Rye to carry him off “struggling in her talons” — a partly jocular image he nevertheless feared as the 19th century turned into the 20th, her success grew, and his mastery waned. Accustomed as he was to being the “biographer” of heroines like Isabel Archer or Milly Theale, it took him years to see the “formidable” Wharton, an attractive, wealthy woman married to an unattractive bully boy , as “trapped” — as his fictive creations were.

But Wharton was. First by her overly protected life, her riches, her beginning writerly identification with him — “The author has been a faithful student of Henry James,” was a typical put-down — and it was relatively late in the game before he began to advise her in useful ways: “Do New York,” he told Wharton, the result eventuating in The House of Mirth, despite the demurrers of her Scribner’s editor, William Crary Brownell. As Richard Lingeman shows in his sensitively amused and warmish portrait of the James/Wharton friendship, Wharton’s Panhard automobile excursions through Europe and North America, afforded James what he wonderfully described as a chance to haul in “a huge netful of impressions,” “fleeing before fate,” crucial for an overweight writer in failing health. He, in turn, encouraged her to experiment beyond her loveless marriage with, among others, the bisexual journalist Morton Fullerton, a true gentleman with an insatiable libido, who made her very happy for a time. James, aged, unable, or unwilling to act on his feelings of attraction for both of them, settled for vicarious fulfillment.

Other literary friendships in Double Lives had bumpier rides. The happier ones included Samuel Clemens and William Dean Howells, and Theodore Dreiser and H.L. Mencken, both writer/editor/critic combinations, founded on practicalities as well as artistic enthusiasm.

Howells, a tiny careful fellow from Jefferson, Ohio, with his eye on literary Boston, snagged a job, first with The Nation, then with The Atlantic Monthly. (He was too shy to actually meet Abe Lincoln, but produced the first bio of the obscure Illinois lawyer for the Republican Party’s original Lincoln presidential campaign.) James Russell Lowell, then editor of The Atlantic, introduced Howells to Emerson, Thoreau, Dr. Oliver Wendell-Holmes, and the banned-in-Boston set, who controlled literary journalism and writing in general in 1860. After a dinner with Howells, the Dr. said of him: “He is like a dim room with a little taper of personality burning on the corner of the mantel.”

Clemens, a tall, red-haired Missouri dude who’d piloted a Mississippi riverboat and gone to California to pan for gold, swam into Howells’ ken via new editor James T. Fields and western cognoscento Bret Harte, who were sure that what The Atlantic needed was blood—“less literature, more life.” Not a problem for Mark Twain, who appeared at a posh French Boston restaurant wearing a sealskin coat with the fur out and his bedhead red coif flaming, regaling the “softs” with tall tales of the western gold camps and Frisco bawdy houses . . . Howells reviewed his The Innocents Abroad and Roughing It, then signed Clemens on for A True Story, which anticipated Huckleberry Finn, and Old Times on the Mississippi, which became Life on the Mississippi.

They worked together for the rest of their lives, their relationship marred only by a doubtfully “jocular” speech Howells arranged for Clemens to make, in which Sam managed to characterize Emerson as “a seedy little bit of a chap”; Holmes as “fat as a balloon,” with “double chins all the way down to his stomach”; and Longfellow as “built like a prizefighter” — all of them drunk and “impostors.” That took several years to live down, and then they fell out over Howells’ withdrawal from a commercial Broadway play they were collaborating on — about a Twain character called “Colonel Sellers,” an over-the-top buffoon from Clemens’ earlier The Gilded Age, who gets involved with scientific gadgetry (some by Thomas Edison!), in such unrelieved slapstick mania that Howells felt three acts of it “would drive the audience into the street,” and make fools of both of them. They overcame that one, too, and lived on for 20 more years of hot Scotch, large cigars, and fine writing . . .

Dreiser and Mencken’s early collaborations — Mencken working as an unofficial reviewer and champion of Dreiser’s post-Sister Carrie work; Dreiser hooking Mencken up with the New York publishing scene, and feeding him little jobs from the ladies’ magazines he was editing — squared with their “managerial” working-class roots. Mencken’s dad owned a cigar factory. Dreiser’s was a failed woolen mill operator. Both were also German-Americans, with shared Teutonic traits: Mencken loved Nietzsche and lager; Dreiser, Schopenhauer and pilsner. Dreiser had a romantic side, longing after the absolute; Mencken was a materialist who horselaughed anything “religious,” and tried to maximize the present. But both were sympathetic to the Kaiser during WWI, and revered craft and hard work.

After things began to pay off for them — Dreiser was a success with nearly everything he wrote after his second novel, Jennie Gerhardt, including The Financier and The Titan, and later The Genius, An American Tragedy, short stories, screenplays, etc., and Mencken rose to eminence as a scathing critic, champion of realism, and editor of The Smart Set and American Mercury magazines — they were matched in the reading public’s mind.

Too closely for Mencken, apparently. He objected to The Genius because it was redolent of Dreiser’s Greenwich Village Bohemian seraglio and its “unhealthy” influence on his friend’s output: the writing was sloppy and self-indulgent, he thought. And there was too much sex. (He fought for the book anyway when it was attacked for “indecency.”) Dreiser bridled under Mencken’s authoritarianism, and criticized The Smart Set (co-edited with George Jean Nathan) as “tamed down”. . . to mere “persiflage and badinage.” Mencken next summed Dreiser up as a great American novelist who sometimes reverted to an “Indiana peasant, snuffling absurdly over imbecile sentimentalities . . .” Dreiser said Mencken “lacked a sense of beauty” and was ‘too materialistic.” Mencken countered that An American Tragedy was “a vast . . . chaotic thing of 385,000 words — at least 250,000 of them unnecessary.” Dreiser: “Who reads you? Bums and loafers. No Goods. We were friends before you were a critic of mine . . .”

They didn’t talk for seven years, but gradually patched it back to civility.

Not the case with F. Scott Fitzgerald and Ernest Hemingway. Hemingway was a serial competitor (Mailer was only junior varsity), going head to head with everyone important in his life — his mother; his “mentor” Sherwood Anderson (who taught him the simple, unliterary prose style he’d learned from Gertrude Stein); his first publisher, Horace Liveright; his second wife, Pauline Pfeiffer; the critic Max Eastman; the Canadian writer and boxing opponent Morley Callaghan; all his subsequent wives; and ultimately, after allowing him to pave the way at Scribner’s for his collaboration with Maxwell Perkins and the publication of The Sun Also Rises, Scott Fitzgerald.

The rivalry was there from the beginning. When they met, Fitzgerald had published The Beautiful and the Damned and This Side of Paradise, and was writing lucrative “flapper” fiction for The Saturday Evening Post, work that simultaneously glamorized and decried gilded American youth in the ’20s. Hemingway had published Three Stories and Ten Poems and in our time, a short sketch collection, for tiny Parisian press runs. But he’d cajoled Edmund Wilson to review him in The Dial, and was cultivating Stein, Ezra Pound, John Dos Passos, etc. He knew he had the goods, and was idealistically pushing a masculine, anti-effete aesthetic that sneered at Scott’s “rich boy stories.” Hemingway, biographer Matthew Brucccoli wrote, “needed a claque, Fitzgerald needed heroes.” Lingeman notes that “Hemingway [had] to dominate and be deferred to; Fitzgerald . . . to charm and be loved.” Hemingway anticipated Gary Cooper and John Wayne; Scott had “the mouth of a beauty,” like the Arrow Shirt Man, and tended to pass out after a few drinks . . . “When I like men I want to be like them. I want to lose the outer qualifiers that give me my individuality . . .” Fitzgerald wrote prophetically.

In Scott’s case, Hemingway’s influence may have stimulated his finest work, The Great Gatsby in 1925, but the next year, The Sun Also Rises established Hemingway as America’s “best author,” and Fitzgerald was henceforth in his shadow. He went on to the end of his days (1940), praising and importuning Ernest to be friends, but Hemingway, as if spurning weakness, disparaged him savagely: he wrote in A Moveable Feast that Fitzgerald, worried about inadequacy, had consulted him on the size of his penis, something unlikely to have happened at all; he accused Fitzgerald, who was refereeing, of letting a boxing round he was losing go on too long, because [Scott] “enjoyed watching” [me] being beaten; he characterized Fitzgerald as “a coward of great charm,” who’d “gone into [a] cheap Irish love of defeat, betrayal of himself, etc.”

Before he died of a heart attack in Hollywood, where he was eking out a living rewriting bad screenplays and drinking, Scott wrote: “I really loved [Ernest], but of course it wore out like a love affair.”

Hemingway told Arthur Mizener, Fitzgerald’s biographer, “I never had any respect for him except for his lovely, golden wasted talent,” and Charles Scribner, their publisher: “Scott was a rummy and a liar and dishonest about money, with the inbred talent of a dishonest and easily frightened angel.”

Lingeman, an editor at The Nation, and the distinguished biographer of Sinclair Lewis and Theodore Dreiser, handles the above, and also the doomed flight of the Beats Jack Kerouac, Allen Ginsberg, and Neal Cassady, with appropriate humor, empathy, and pathos. He matches the arcs of his writers’ personal lives with the larger arc of the cultural history of the last 150 years.

— John Lombardi