Rum. Caribbean. Anti-hero. Depp. Tick off each item on that checklist, you’ll notice that The Rum Diary, opening today, shares several key elements with the adventures of a certain Caribbean pirate Captain.

While tired old seadog Jack Sparrow will no doubt be popping up at any number of Hallowe’en costume parties this weekend, he will not be putting in an appearance on the big screen. Instead, Johnny Depp spins another new take on a different movie brand with which he has become strongly entwined: the persona of late gonzo journalist Hunter S. Thompson.

Diary, a stylish ’50s era quasi-thriller, is the long-awaited film adaptation of Thompson’s novel of the same name. How long awaited? About five decades. Thompson originally wrote The Rum Diary in the early ’60s and failed to find a publisher. He finally got the book into print in the late ’90s, only to see the film version trapped in development hell for the duration of his life.

How does someone with Thompson’s famously uneven-keeled demeanour respond to Tinself-town stagnation? This 2001 memo from HST to the production company that had the film rights at the time suggests that aggression is the choice tactic. “It’s like the whole project got turned over to zombies who live in cardboard boxes under the Hollywood freeway.”

Now, with the film’s release, Thompson’s ghost gets the last ether-infused laugh. The story follows the escapades of reporter Paul Kemp, who finds himself mingling with low-lifes living the high life in mid-century Puerto Rico. Kemp gets swept up in a tropical storm of booze, money and infidelity as he tries to figure out whether to use his journalism to expose or profit from the schemes of wealthy developer Sanderson, played by Aaron Eckhart.

Like Thompson’s best journalism, this fictional tale is at least loosely based on the writer’s real experiences. And, as with his best-known work, Fear and Loathing in Las Vegas, Thompson sees his gonzo craziness channelled into Depp as uncanny avatar.

Never mind the weighty questions that Diary touches on, including addiction, ethics, and quasi-colonial exploitation: Let’s stick to the superficial. Diary marks one of those few occasions since teen-cop TV show 21 Jump Street where Depp plays a guy from whom you might actually to take some fashion pointers. Edward Scissorhands Depp? No. Willy Wonka Depp? No. Ed Wood Depp? At least half the time, no. Sweeney Todd Depp? Mad Hatter Depp? Real-life Depp, with the long, lank hairdo, bad hats, and Zorro ’stache? Hells no.

The fact is, when Depp copped Thompson’s signature look for Fear and Loathing — the Hawaiian shirts, short shorts, white socks and fishing hat — it was a style upgrade for the actor. This rum-soaked Kemp fellow from Diary, with the hair pomade, the collars spread over blazer lapels, the skinny ties, the round-the-clock sunglasses? Alcoholism or no, here is a dude who can dress. We can drink to that.

The idea that even a fictionalized Hunter S. Thompson could become a sartorial inspiration, rather than a cautionary tale? Well, that’s not just strange — that’s straight out of bat country. Come to think of it, we can drink to that, too.

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Image courtesy of Entertainment One.