Tales Of The City by Armistead Maupin (1978)
Maupin’s easy-going snapshots of San Francisco life (there are nine books in total, ranging from 1978 to 2014) have an appealing, high-definition soap opera quality but their ground-breaking representations of gender and sexuality also exemplify the progressive spirit of the city. Escapist literature at its most gentle and delightful.
Homeboy by Seth Morgan (1990)
Morgan’s only novel — he died at the age of 41 — offers a rather different take on San Francisco: it’s a pummelling, gritty story set in the city at the height of the Aids epidemic, which follows a strip joint barker’s hellish journey into prison. The events Morgan depicts may be depraved but his luminous prose is anything but.
A Walk On The Wild Side by Nelson Algren (1956)
A neglected classic, Nelson Algren’s novel (which lent its title to the Lou Reed song) follows the adventures of an illiterate redneck amid the messy underworld of pimps, barflies and drop-outs in Depression-era New Orleans. Algren’s writing is so startling beautiful it inspired envy in Ernest Hemingway.
Coming Through Slaughter by Michael Ondaatje (1976)
Michael Ondaatje is known most for The English Patient but for my money this is his best book — a freewheeling experimental novel that summons the delirious spirit of New Orleans’ early 20th-century jazz scene through the life of pioneering cornet player Buddy Bolden. An elusive, shape-shifting novel that at times feels as improvised as jazz itself.
The Age Of Innocence by Edith Wharton (1920)
The morally conservative gilded lives of New York’s upper classes in the 1870s is brought to wrenching life in Wharton’s loosely autobiographical novel about Newland Archer, trapped in a joyless marriage and desperately in love with another woman. Effervescently written, it’s particularly fabulous on the stifling hypocrisies of late 19th-century New York high society.
A Little Life by Hanya Yanagihara (2015)
If you’ve been putting off reading Yanagihara’s mighty novel about four friends who move to New York because you haven’t had the time (it’s over 700 pages long), that excuse has just busted its sell-by date. Everyone I know who has read this has raved about its uncompromising depiction of suffering and survival in a city in which a happy and successful life is regarded as mandatory.
Native Son by Richard Wright (1940)
This uncompromising story of a poor black man who kills a rich white woman in a moment of panic made Wright the first bestselling black author in the US. A viscous indictment of the brutalising impact of poverty on black urban communities, it’s not an easy read but its atmosphere of racial distrust in the Windy City remains as resonant as it ever was.
The Death Of The Detective by Mark Smith (1974)
A grief-stricken detective’s dogged pursuit of a crazed killer takes the reader on a hallucinatory odyssey through the rot of post-war inner-city Chicago in this heavily stylised, slow-burning thriller.
Less Than Zero by Brett Easton Ellis (1985)
Ellis’s debut novel set among the obscenely wealthy, obscenely bored rich kids of LA in the ’80s is almost too good at depicting the moral nihilism of the times: to read it is to be left feeling almost as empty as its characters’ lives. Yet Ellis’s blankly mesmeric descriptions of casual sex and drug-taking remain as evocative a snapshot as any of LA’s hollow, rapacious soul.
This Book Will Save Your Life by AM Homes (2006)
A heart attack and the appearance of a swamp hole outside his house are the two events that prompt divorced trader Richard Novak to wonder whether his efficient solitary life is the best way to live after all. Homes tracks Novak’s journey back to emotional life with wit and affection in a novel that also serves as a love letter to LA’s beguiling weirdness.
Fear and Loathing in Las Vegas by Hunter S Thompson (1971)
A cornerstone text of gonzo literature, this whacked-out head trip into the profane underbelly of the American dream is based on his own drug-crazed visit to the city the same year. Combining ruminations on ’60s counter-culture with surreal encounters with cops and casino operators, it’s both grotesquely funny and nightmarishly bleak.
Leaving Las Vegas by John O’Brien (1990)
You probably know this novel for the Nicolas Cage film from 1995 but John O’Brien’s original is well worth reading too. It’s a terribly sad and unnerving story of alcoholism and despair played out in the neon glare of Las Vegas’ casinos. O’Brien committed suicide in 1994, aged only 33.
Their Eyes Were Watching God by Zora Neale Hurston (1937)
A neglected voice of the Harlem Renaissance, Hurston is rightly being rediscovered by a generation hungry for representations of black lives. This is a remarkable account of a female slave descendant’s fight for autonomy.
Tourist Season by Carl Hiaasen (1986)
If there is a modern poet laureate of Florida, it’s Carl Hiaasen. His demented capers are both perversely entertaining and barely concealed satires of the Florida swamp, shamelessly peopled by property scammers, rampant developers and corrupt officials. This novel, a garish comedy about a reporter turned private eye on the trail of a serial killer, is his first.
The Bostonians by Henry James (1886)
A big, bustling novel of ideas, described by its author as a ‘very American tale’, Henry James’s comic realist masterwork is both an excellent study of a city in the aftermath of the American Civil War and a savagely witty critique of sexual politics. James’s novels can be tough to penetrate but since we’ve all got a bit of time on our hands, it’s worth persevering.
The Given Day by Dennis Lehane (2008)
Set in Boston in the early 20th century, Dennis Lehane’s teeming novel shows Boston at a point of tumultuous change, riven by police strikes, union agitation and anarchist politics. Lehane was a part-time writer on The Wire and his novel has a similar wide-screen filmic feel.