Hollywood’s most baffling casting choices

So, Woody Allen - lovable, neurotic, buffoonish intellectual Woody Allen - has been cast as, umm, a pimp, in new movie ‘Fading Gigolo’.

It’s an off the wall casting decision, but not without precedent in Hollywood’s murky past. Here are the casting choices that we still can’t quite believe were actually given the go-ahead by cigar-chomping Hollywood bigwigs.

[Related story: Woody Allen lands first major role in 12 years... as a pimp]

Dustin Hoffman and Warren Beatty in ‘Ishtar’

For this big budget comedy, a bumbling loser and an assured ladies man were required. Dustin Hoffman and Warren Beatty were duly cast… but the wrong way round. Director Elaine May thought it would be funny if notorious womaniser Beatty and ‘Graduate’ star Hoffman played against type. It wasn’t, and the film was a bomb.

Tara Reid in ‘Alone in the Dark’

Denise Richards’ Dr. Christmas Jones (in ‘The World is Not Enough’) is often cited as Hollywood’s least convincing academic. But for our money Tara Reid – of ‘Celebrity Big Brother’ fame - was an even worse boffin. She played an archaeologist and museum curator in terrible video game adaptation ‘Alone in the Dark’, but spent most of the running time baring her midriff.

Tony Curtis in ‘The Black Shield of Falworth’

Tony Curtis was the streetwise kid from the Bronx who became a legend for ‘Some Like it Hot’, ‘The Sweet Smell of Success’ and ‘The Defiant Ones’. One of his less successful roles was playing a 15th century knight in this epically shoddy historical dirge. Curtis may not have actually said the infamous line ‘Yonda stands da castle of my fodda’, but he did deliver much of his dialogue with a distinct New York twang. Unconvincing.

Kevin Costner in ‘Robin Hood: Prince of Thieves’

Without doubt ‘Robin Hood: Prince of Thieves’ is a guilty pleasure: Alan Rickman’s Sheriff of Nottingham, Mortianna the mad witch, the bit where the blokes shouts “to the trees!”. But there’s no denying the film has a beige, charisma-free hole at its centre thanks to Costner as Robin himself. Check out Errol Flynn’s thigh-slapping antics in the 1938 version for how to do Hood properly.

Katherine Hepburn in ‘Dragon Seed’

Not even Katherine Hepburn’s sack full of Oscars could convince us that she was a heroic Chinese woman called Jade who leads a village in an uprising against evil Japanese invaders. This blatant slice of war time propaganda (it was made in 1944) just feels a bit wrong today.

Vince Vaughn in ‘Psycho’

To be honest, Gus Van Sant’s weird shot-for-shot ‘Psycho’ remake was misjudged in virtually every respect. But casting funnyman Vince Vaughn – yep him out of ‘Wedding Crashers’ – as mum-loving nightmare Norman Bates was possibly the worst decision of all. Just watch the original.

Bruce Willis in ‘The Bonfire of the Vanities’

It’s a crying shame that the movie version of Tom Wolfe’s amazing book – which expertly skewers the ‘greed is good’ culture of the 1980s – was scuppered by unbelievably duff casting.  Firstly promiscuous Wall Street slimeball Sherman McCoy was played by, err, America’s nicest man Tom Hanks. Then Bruce Willis somehow landed the part of sleazy hack Peter Fallow, who was English in the book but American in the film. Perhaps the infamously truculent Willis couldn’t be bothered to do an accent.

Colin Farrell in ‘Alexander’

Firstly, that bloody wig. Who knows if the real Alexander was blonde, but we imagine him thus, so Farrell was forced to don the least convincing hairpiece since John Travolta’s in ‘Wild Hogs’.  He didn’t drop the Irish accent either, or that permanent, slightly confused look of his that worked so well for ‘In Bruges’, but didn’t feel quite right for the most successful military commander of all time. 

John Wayne in ‘The Conqueror’

Perhaps the most surprising piece of casting OF ALL TIME.  All-American icon John Wayne donned a silly moustache to play Mongolian warlord Genghis Khan in a film widely regarded as one of the worst ever. The Duke delivered shockers like “I shall keep you, Bortai, in response to my passion” in his trademark drawl. Co-star Susan Hayward looked embarrassed throughout.

What other casting decisions left you baffled? Please let us know in the comments below…