Founded by gold-rush squatters, and reshaped by a huge influx of black workers from the South during the Second World War, it has been consistently outshone by its urban neighbours. Berkeley, internationally famous as a centre of learning and student dissent, is just up the road. San Jose, the hub of booming Silicon Valley, is 30 miles to the south.
Jerry Brown, the state's former governor, may feel a little as Oakland does. Something of a boy genius when he was elected to the governorship at the age of 36, he became a spent politician after three abortive runs for the White House and two for the California Senate. Now, he is running for mayor of Oakland.
Since Mr Brown announced his candidacy last year, he has been riding high in the polls, and grudgingly welcomed even by his opponents as a figure to put Oakland, for once, on the map.
"The city has a huge inferiority complex," said Stacey Wells, a political writer for the Oakland Tribune. Her paper has noted that Brown has, albeit temporarily, made Oakland "the centre of the universe", drawing national and international notice.
Mr Brown, who turned 60 last week, trained as a priest as a young man, sat at the feet of Mother Teresa and dabbled in Zen Buddhism. He was christened "Governor Moonbeam" for once suggesting that California launch its own space station; the nickname stuck.
He is the scion of California's most famous political family. His father, Pat Brown, was a two-term governor, and his sister ran for governor in 1994. But Jerry has not won an election in 20 years. He became a bad penny in Democratic politics, an ageing iconoclast who hectored other candidates - most notably Bill Clinton - for selling out to special interests. He quit the Democrats two years ago, saying political parties were just "marketing labels", and is running on an independent ticket.
Oakland, meanwhile, has suffered much for Gertrude Stein's observation, more than 60 years ago, that "there is no there, there". It has also struggled to recover from a 1989 earthquake, disastrous fires in 1991, high crime rates and poor schools.
Mr Brown's campaign agenda is vague - critics say he will be crushed by the grind of local politics - but he has promised to make Oakland a "sparkling city on the hill", claiming cities are now "the place we can rejuvenate American politics".