Back in the day, when Donald Trump would appear on TV shows, rather than lie in bed and tweet about them, he had a love-hate relationship with Conan O’Brien.

He loved the attention, but he hated the fact that Conan wasn’t afraid to take the piss out him, which his fragile ego just couldn’t stomach.

During his first appearance on The Conan O’Brien Show, way back in 1997, Donald was asked about how much cash he had in his pocket.

Perhaps we shouldn’t be surprised that he thought it would be funny to whip out a condom:

Safe sex, said the guy who allegedly slept with Stormy Daniels without using a condom, while his wife was pregnant with his son.

As it turns out, that exchange above actually left Donnie fuming, as Conan recounted when talking with Rolling Stone:

He was pissed. He was really mad. I went to commercial. He stood up. I don’t think he said goodbye to me, and he walked over to my producer and said, “That’s the last time I’m gonna be on this fucking show. He humiliated me in front of everybody.” He stormed out. Cut to me seven more times [over the years]: “Ladies and gentlemen, Donald Trump!” He got over it, clearly.

He would shoot bits for us: “Can we get Nipsey Russell to come shoot something? He’s not available? Well, then try Donald Trump. Donald will do it.” Anyone who would do that, and then is the leader of the free world, is not going to make sense to me.

You’re not alone there, Conan.

During another appearance on the show, Donald tried to improvise while taping a bit called “Secrets”. Much like his speeches, where he abandons the teleprompter and begins to talk utter shite, it wasn’t a good look:

If only his sense of humour, or lack thereof, was the world’s biggest gripe.

Then again, this is a man who regularly commented on his daughter’s attractiveness, thinking it was funny. Other than the truly weird intro and outro in the video below, this is on the money:

Ah yes, the hilarious ‘sex with my own daughter’ gag.

[source:rollingstone]