Johnny Depp in The Rum Diary: Yo Ho Huh?

The Pirates star takes a break from kid-centric movies to honor his old pal Hunter Thompson with this louche, fitfully appealing comedy

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Peter Mountain / FilmDistrict and GK Films

Giovanni Ribisi, Johnny Depp and Michael Rispoli in The Rum Diary

“I tend to avoid alcohol when I can,” says Kemp (Johnny Depp), a reporter who has just joined an English-language newspaper in San Juan, Puerto Rico. Actually, he tends to avoid not drinking. Calibrating his liquor consumption as “at the upper end of social,” Kemp hitches an occasional ride on the wagon, then gets off and brags, “I finally beat my will power.” When he goes on a toot at a bowling alley, the tenpins morph into rum bottles. San Juan in 1960, when Kemp arrives, is a territory pining for statehood (which Hawaii and Alaska had just achieved) and shivering at the recent Communist takeover of Cuba, 1,100 miles across the Caribbean. But the locals don’t figure nearly as importantly in Kemp’s adventures as booze does. The movie is, after all, called The Rum Diary.

The trajectory of Johnny Depp’s career could be both an inspiration and a cautionary tale for Hollywood rebels. The young Depp was as wayward as he was beautiful. Graduating early from entertainment’s mean Streets (TV’s 21 Jump, Wes Craven’s first Nightmare on Elm), he flew in early manhood toward the weird and the serious. Count the ways: after a bit in Platoon, Depp starred as the greaser in John Waters’ Cry-Baby, the fish-tagger in Serbian director Emir Kusturica’s Arizona Dream, the Buster Keaton wannabe in Benny & Joon, Leonard DiCaprio’s protective brother in What’s Eating Gilbert Grape, the shear-fingered or blithely demented Eds of Tim Burton (Scissorhands, Wood), the hapless bookkeeper in Jim Jarmusch’s black-and-white “acid Western” Dead Men, the gypsy horsemen in Sally Potter’s The Man Who Cried and cocaine king George Jung in Blow. In 1997 Depp directed himself and Marlon Brando in The Brave, a gorgeous, suicidally obscure modern-day Western sadly unavailable on Region 1 DVD. He capstoned his Weird Phase by playing Hunter Thompson’s alter ego (and libido) Raoul Duke in Terry Gilliam’s 1998 film of Fear and Loathing in Las Vegas. All in all, an imposing résumé, boasting its fair share of daring.

Around this time Depp settled down in France with actress Vanessa Paradis and raised their two children. Since then he’s made movies mostly for his kids: the four Pirates of the Caribbean megahits, Finding Neverland, Alice in Wonderland, Rango. Nothing against some of these films, but they denied Depp his lingering musk of danger. Over this same span, George Clooney, another dreamboat star, fronted grownup movies, the kind he’d like to see. All right, Clooney is a serial bachelor, with no responsibility to amuse his spawn on screen as well as at home. But Brad Pitt, who like Depp lives with a famous actress and has some kids, took career risks with Babel, Burn After Reading, The Assassination of Jesse James by the Coward Robert Ford and The Tree of Life. Depp needed some offbeat project, if only so he could radiate something besides mad or weary brio in G or PG-rated pre-tween fare.

He found his respite from Jack Sparrow in an early novel by his old pal Thompson, who died in 2005. (Depp arranged the cannon that shot Thompson’s ashes into the Pacific.) The actor bought the rights and convinced a character nearly as eccentric as Thompson to adapt and direct it. The Englishman Bruce Robinson began as an actor (Benvolio in Franco Zeffirelli’s 1968 Romeo and Juliet, the dashing Lieutenant Isabelle Adjani is mad for in François Truffaut’s 1975 The Story of Adele H), then a decade later put part of his own life on film with Withnail & I, a memoir of himself and a sublimely inebriated flatmate played to haughty-pathetic perfection by Richard E. Grant. Over the years Withnail has been deeply cherished—Depply cherished, too. The star saw an Alcoholics Enormous kinship in Robinson and Thompson, and produced The Rum Diary, with Robinson directing, in Puerto Rico in early 2009. Nearly three years later, here it is.

(MORE: See Withnail and I in the Top 10 Sloppiest Movie Drunks)

“Puerto Rico was a backwater and the Daily News was staffed mainly by ill-tempered wandering rabble,” Thompson writes in an essay accompanying the book. “In a sense I was one of them — more competent than some and more stable than others — and in the years that I carried that ragged banner I was seldom unemployed … I wrote ad copy for new casinos and bowling alleys. I was a consultant for the cockfighting syndicate, an utterly corrupt high-end restaurant critic, a yachting photographer and a routine victim of police brutality. It was a greedy life and I was good at it. I made some interesting friends, had enough money to get around, and learned a lot about the world that I could never have learned in any other way.”

Thompson poured his life into his novel. Kemp’s first assignment is covering the bowling scene; he is offered a job writing copy for hotel-casinos about to be built on an island abandoned by the U.S. military; his friend Sala (Michael Rispoli) makes side money, sometimes big money, in cockfights; he hitches a ride on a rich American’s yacht; he earns the suspicions of local toughs and the police. Kemp’s temptations include promised millions in a scam dreamed up the American ex-journalist Sanderson (Aaron Eckhart) — a modern pirate of the Caribbean who calls the island “God’s idea of money” and has a racist aversion of “the overtanned locals” — as well as the blond warmth of Sanderson’s mistress Chenault (Amber Heard).

The Rum Diary and Withnail & I have this in common: they’re louche — a word I have to look up every time I think of using it, but which means appealingly disreputable. Thompson’s plot suggests a Grahame Greene novel of comic espionage, like Our Man in Havana, transferred to San Juan and given a Mickey Finn. Proudly sodden and sleepy-eyed, the movie plays like a drunken night with the guys as seen by the one teetotaler; it displays the amiability of an alcoholic haze without conveying it. Robinson is sharper with the scene of Kemp and Sala trying some LSD-type wonder drug. (Kemp stares at his friend, notices something odd protruding from his mouth and says, “Your tongue—it’s like an exploratory gibbet.”) They got the drug from Moburg (Giovanni Ribisi), their severely delusional colleague at the paper, who’s prone to observations like “Did you see the side of his neck? Blackheads like Braille.”

Set in 1960, The Rum Diary has the grainy look and grungy feel of a ’70s dark comedy like Where’s Poppa? or Little Murders — movies that pursued misanthropic satire and didn’t care if anybody got it. This sense of a film that’s one decade off is reinforced by the characters’ use of words (vibe, Jacuzzi, condo) that didn’t enter common usage until the end of the ’60s. It’s pleasant to spend time back in the day, whatever the year, and to slip into the skin of a movie perfectly content to let its audience observe behavior without having to accept it. Maybe too content. Sanderson says that “Some days are two sizes too small”; the movie is too, defiantly tiny, an agreeable time-waster for the onlookers and its star. The Rum Diary isn’t a corrective to Johnny Depp’s kid-centric career, more like a vacation from it, in a resort where the visitors are strange, the natives are restless and the flow of alcohol endless.

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