Donald Trump's most awkward movie cameos

As hard as it is to fathom now, before becoming the leader of the free world, President Donald J. Trump was an eccentric and slightly bizarre c-list celebrity, thanks primarily to his real estate empire and role as chief hirer and firer in the US version of ‘The Apprentice’.

Over the years he appeared on the small screen countless times, but he was no stranger to the big screen either.

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Trump’s Hollywood career included a handful of weird silver screen cameos alongside the likes of his former friend and now fierce critic Whoopi Goldberg, child star Macaulay Culkin and, of course, Hugh Grant. 

Here we rank the most awkward of these scene-stealing performances... 

The Associate (watch Trump here - 1:54)

This is special. As he’s spoken to, Trump is so distant and seems so disconnected from what’s going on that you’d believe someone if they told you he had been added in with CGI post-production.

Instead of reacting to a word being said to him, he looks at his watch like a nervous extra asked to act casual then seems to look right down the camera when the scene moves away.

Whoopi Goldberg’s character then appears, ignoring Trump completely only for him to quickly follow her. Very awkward, very strange.

'Ghosts Can’t Do It’ (watch Trump here)

In 'Ghosts Can’t Do It’, Bo Derek plays a widow who conspires with the ghost of her dead husband Scott (who only she can see) to have a young man drown so Scott can claim his body and come return to the world of the living.

It is not very good.

Donald Trump plays himself, sharing several oddly flirty scenes with Bo Derek, who at one stage says he is “too pretty to be bad”. He also gently caresses a scale model of a boat for some reason (see above).

'The Little Rascals’ (watch Trump here - 2:24)

In 'The Little Rascals’ Trump plays a crazy-rich oil tycoon who pops up to tell his son, who is riding a super-expensive soapbox kart and has his own mobile phone, that he’s “the best son money can buy”.

Pure Trump. Did he purchase the child at a young age? It’s not clear, but the boy (called Waldo, obviously) seems happy enough with the compliment.

It’s Trump’s unruly eyebrows that are the real stars here however. You can see them at the top of this article. 

'Two Weeks Notice’ (watch Trump here)

It’s hard to tell in this clip, in which Trump talks to Hugh Grant’s character about recently being dumped by Sandra Bullock’s lawyer, whether he’s doing so from a place of friendly concern or ridicule.

The latter would be more believable, but the mixture of Trump’s acting and Hugh Grant’s enormous, distracting tie (we’ve forgotten why he’s wearing it in the film, there must be a reason) make it hard to tell.

'Eddie’ (watch Trump here - 2:42)

In 'Eddie’, Whoopi Goldberg plays the titular New York limo driver: a hardcore Knicks fan who, with a certain amount of luck, becomes head coach of the famed basketball team.

In Trump’s cameo, the future president claims hiring Eddie was his idea from the very start. Not the last lie he’d ever tell in front of camera.

'Home Alone 2: Lost in New York’ (watch Trump here)

In Trump’s most famous big screen appearance, he helps guide Macaulay Culkin’s burglar-traumatising Kevin McCallister to the lobby of New York’s Plaza Hotel - which he owned at the time.

It’s an innocuous little gag about Kevin not knowing who Trump is, but it’s made just a little awkward by how long the magnate spends hanging around in the background of the shot, making sure everyone in the audience sees him. 

'Zoolander’ (Watch Trump here)

'Zoolander’ is loaded with incredible cameos, but Trump’s isn’t one of them. That’s no criticism though, Billy Zane and David Bowie are stiff competition.

'Trump’ appears at the very start on the red carpet for a major awards ceremony in the fashion industry. He’s one of the host of faces that pays tribute to Ben Stiller’s legendary male model.

Picture Credits: Warner Bros / Universal Pictures / Triumph Releasing / 20th Century Fox