Sinead O’Connor v Arsenio Hall: Watch Their 1991 Spanking Flirtation (Video)

Today, he’s suing her for libel — but on Hall’s show, they flirted awkwardly and adorably

Last Updated: May 5, 2016 @ 4:17 PM

Arsenio Hall is currently suing Sinead O’Connor for libel, but 25 years ago they had a charmingly flirtatious relationship: O’Connor joked about Hall spanking her during a 1991 interview on “The Arsenio Hall Show.” He called her “a very attractive woman.” She near-whispered back that he was “gorgeous.”

And then it all went to hell.

Hall sued O’Connor Thursday after O’Connor wrote a Facebook post accusing him of providing Prince with drugs, and called him “Prince and Eddie Murphy‘s bitch.” She also said she had reported Hall to Carver County, Minnesota authorities investigating Prince’s April 21 death, and accused Hall of drugging her at some point.

“They are aware you spiked me years ago at Eddie Murphy‘s house. You best get tidying your man cave,” wrote O’Connor, whose biggest hit, “Nothing Compares 2 U,” was written by Prince.

Hall fired back in his lawsuit that she was “now known perhaps as much for her bizarre, unhinged Internet rants as for her music.”

It’s easy to forget that in the early 1990s, O’Connor’s appearances on Hall’s talk show were the stuff of late-night legend. “The Arsenio Hall Show” was the hottest in late-night, in part because of his easy banter with guests. In one appearance, O’Connor described how she resisted a record company’s pressure on her to get an abortion, and about her unabashed love for rap groups like N.W.A.

In another interview, she talked about a British critic who said she should be spanked. Hall saw an opportunity.

“Can you give me his number? In case y’all work it out, I’d like to do the spanking,” he said.

“I’d like to,” she smiled. “I was gonna ask you if you would, actually.”

“Let’s get busy,” he said.

“What are you doing later on?” she replied, rubbing the back of her famously shaved head. (It starts at the five-minute mark in the video above.)

Later in the same interview, Hall also pressed O’Connor on her insistence that she often considered herself “ugly and hideous.” (It’s at the 11:30 mark.)

“Every girl goes through phases of feeling like a dog,” she says, confessing that she even feels that way during the interview.

“Stop,” says Hall. “Don’t you realize that you can’t cut your head bald and look this beautiful if you’re ugly and hideous? You’re a very attractive woman.”

Hall’s audience applauded.

“I feel better now since you think I’m attractive,” she answered. “A lot of Irish people, me included, we have problems with our bodies, a problem with feeling good about ourselves. It takes someone as gorgeous as yourself to say it before they believe it.”

“Yeah, right,” laughed Hall.

They also talked about going to a Lakers game. It was unclear whether that ever happened, and what happened at Murphy’s house. But at some point, in the next 25 years, the flirtation came to a hard stop. And now they find each at opposite ends of a lawsuit, battling over the life and death of a music legend.