That's the question Ian Buruma asks in this piece in The Sunday Times (via Arts & Letters Daily):
One of the most vexing things for artists and intellectuals who live under the compulsion to applaud dictators is the spectacle of colleagues from more open societies applauding of their own free will. It adds a peculiarly nasty insult to injury.
Buruma runs through some well-known examples of tyrants who have felt such love, including Stalin, Mao, Pol Pot, and Castro ("Last year a number of journalists, writers and showbiz figures, including Harold Pinter, Nadine Gordimer, Harry Belafonte and Tariq Ali, signed a letter claiming that in Cuba 'there has not been a single case of disappearance, torture or extra-judicial execution since 1959…'"). And now, Venezuela's Hugo Chavez ("not yet a Castro, let alone a Pol Pot"), despite his restricting speech, quashing dissent, and more.
What motivates this longstanding dynamic?
The common element of radical Third Worldism is an obsession with American power, as though the US were so intrinsically evil that any enemy of the US must be our friend…
Criticism of American policies and economic practices are necessary and often just, but why do leftists continue to discredit their critical stance by applauding strongmen who oppress and murder their own critics? Is it simply a reverse application of that famous American cold war dictum: "He may be a bastard, but he's our bastard"? Or is it the fatal attraction to power often felt by writers and artists who feel marginal and impotent in capitalist democracies? …
When democracy is endangered, the left should be equally hard on rulers who oppose the US. Failure to do so encourages authoritarianism everywhere, including in the West itself, where the frivolous behaviour of a dogmatic left has already allowed neoconservatives to steal all the best lines.
"Thank you, my foolish friends in the West" here.