Best known for his 1971 autobiographical novel Fear and Loathing in Las Vegas, Hunter. S. Thompson owned this 1973 Chevrolet Caprice from 1990 until his death in 2005, naming it the “Red Shark” in tribute to the original “Great Red Shark” driven by his alter ego Raoul Duke in his most famous work. A roman à clef, written in the gonzo journalism style that Thompson helped popularise, the story followed Duke and his attorney Dr. Gonzo on a road trip to Las Vegas in the Great Red Shark to chase the American Dream through a frenzied, drug-fuelled haze. First published as a two-part series in Rolling Stone magazine in 1971, the plot was a blend of fact and fiction, based on two trips that Thompson took to Las Vegas with attorney and Chicano activist Oscar Zeta Acosta in March and April 1971, and served as a eulogy for the failed counterculture movement of the 1960s. The Great Red Shark of the novel was a large Chevy convertible rented by Duke and Gonzo for their trip and served as a symbol of American capitalist culture and the American Dream. Old elephants limp off to the hills to die, writes Thompson in the novel ; old Americans go out to the highway and drive themselves to death with huge cars. A benchmark of 1970s American literature, the novel was adapted into a 1998 film of the same name by director Terry Gilliam, starring Johnny Depp as Raoul Duke and Benicio del Toro as Dr. Gonzo.

Thompson received this 1973 Chevrolet Caprice as a gift from notorious West Coast porn impresarios Jim and Artie Mitchell in 1990. Thompson had befriended the Mitchell brothers in the mid-1980s, when he spent a period of time working as the night manager at their San Francisco adult cinema, the O’Farrell Theatre – which he described as the Carnegie Hall of public sex in America – while purportedly researching a story on feminist pornography for Playboy and working on a book for Random House to be titled The Night Manager, neither of which projects ever materialised. The Mitchells made a 30-minute documentary about him in 1988, titled Hunter S. Thompson: The Crazy Never Die. When Thompson was arrested and charged with possession of drugs and explosives in 1990, the Mitchell’s reportedly showed their support for the beleaguered journalist by restoring a 1970s Chevrolet Caprice Convertible, similar to the model driven by Thompson’s protagonist in his famous 1971 novel, and led a caravan to Colorado to coincide with his preliminary hearing, which was ultimately called off when prosecutors dropped the charges.

Thompson’s 2003 book Kingdom of Fear included an extract from local newspaper the Times Daily, dated 22 May 1990, which reported: On the eve of his preliminary hearing on drug charges, author Hunter S. Thompson rejected a plea bargain offer from prosecutors and received a red convertible from well-wishers who travelled here from San Francisco. His supporters, led by porn theatre owners Jim and Art Mitchell, left the Bay Area in a convoy of a half dozen vehicles at 3 A.M. Sunday… They said they came to Aspen to support Thompson, who wrote about the government’s unsuccessful 11-year battle to shut down their establishment… [a member of the convoy] said the only problem during the road trip was on Interstate 80 near Truckee when a California state patrolman stopped the convertible that was later given to Thompson. In the backseat was a 3-foot-tall stuffed buffalo head that was also given to Thompson on Monday in memory of the movie and book “Where the Buffalo Roam”.

Naturally, Thompson would nickname the car the “Red Shark” after the infamous Great Red Shark from Fear and Loathing, and it would go on to appear on the back cover of his 1994 book Better Than Sex: Confessions of a Political Junkie, and the front cover of his 2004 collection of articles Hey Rube: Blood Sport, the Bush Doctrine, and the Downward Spiral of Dumbness. Earlier in the aforementioned Kingdom of Fear, Thompson refers to his trusty Red Shark, a rebuilt 1973 454 Chevy Caprice with power windows and heated seats and a top speed of 135. Several friends and associates have written of their adventures with Thompson in his red Caprice over the years. Former Esquire editor Terry McDonell recounts that Hunter liked to play host - even picking you up at the airport in the ’71 Chevrolet Impala convertible he called the “Red Shark”. Ralph Steadman, who famously illustrated Thompson’s original novel, describes a thrilling near-death episode with Thompson at the wheel in his 2006 memoir, in which the Red Shark morphed itself into a switchblade and slipped through the gap that wasn’t there, adding, It was not luck, nor good management, nor even divine intervention. The Red Shark was liquid. On a timeless thread, a gossamer wing, it took on a life of its own and animated itself to emerge like a smear of red cellulose into the open and on down the road.

Steadman also devoted a passage to describing Thompson’s treasured vehicle as such: the Red Shark, a restored seventies Chevy… dazzled glamorously in the high altitude light; its rear, svelte buttocks thrusting back contemptuously towards the vehicle it had just passed on the inside hard shoulder. The expansive beige/crème sofa seats warmed luxuriously in the sun. Set up beside the four-speed manual gear-shift was Hunter’s pièce de resistance – a polished walnut drinks tray taken from some elegant, long-gone Rolls Royce. It was large enough to hold a wide glass of scotch on the rocks, another glass of spare ice and a bottle of Heineken.

Thompson’s Chevrolet Caprice was one of two cars used during production of the 1998 film to represent the Great Red Shark. After living with Thompson for several weeks to immerse himself in the character and study his motivations and mannerisms, Johnny Depp reportedly drove the car himself from Thompson’s home in Colorado to Los Angeles for the production and back again. Depp copied notebooks, taped conversations and even dug out much of Thompson’s 1971 wardrobe, reported Rolling Stone magazine’s Chris Heath in 1998. Finally, Thompson let him take the Red Shark, the Chevy convertible that features in the film, back to Los Angeles. Depp left Woody Creek at 3 a.m. in the freezing cold. The car's top was stuck down, its motor broken. Thompson – “he was really being very paternal at this point,” says Depp – gave him some flashlights and a cooler packed with essential supplies. He listened to a portable tape recorder – as Thompson and Acosta had on the original trip – playing songs that Thompson mentions in the book.

While a red Chevrolet Impala was used for exterior shots, Thompson’s Chevrolet Caprice was used for many of the interior shots in Fear and Loathing in Las Vegas, most notably during the opening sequence in which Duke and Gonzo load up the convertible with illicit drugs and drive from LA to Las Vegas on LSD, scaring off a hitchhiker en route. The car’s steering wheel was replaced at some point in the production with a steering wheel from a Chevrolet Impala, presumably for continuity purposes during filming. The car was also used for interior shots during the police chase outside Baker, California, when Duke first attempts to leave town. While the film polarized critics on its release, it has come to be regarded as a cult classic.