Rosie O’Donnell got into Donald Trump’s orange head on Kimmel: ‘I know you're watching’

Twenty-four years ago, Rosie O'Donnell sat behind a talk-show desk calling every attractive man who crossed her stage a "cutie patootie," a running bit that became her signature even as most of America had already put two and two together about the woman delivering it.

In 2002, the year The Rosie O'Donnell Show ended its run, O’Donnell came out as a lesbian, and The Advocate promptly named her its Person of the Year.

She's been one of ours, and one of ours here at The Advocate, ever since. Soon after she came out, she became a regular contributor to our magazine. Further, she has fiercely advocated for equal gay adoption and foster rights, co-created the pioneering R Family Vacations company for queer families, and continuously uses her platform to support LGBTQ+ youth, artists, and inclusive parenting.

This week, she proved she hasn't lost a step.

Last night, O'Donnell guest-hosted Jimmy Kimmel's show while Kimmel takes his annual summer break. And she picked up right where she left off more than 20 years ago. In fact, you might even say that, like a fine “cutie patootie” George Clooney, she has gotten better with age.

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"They said you can't come home again, but here I am," she told a standing, cheering studio audience, before warning, "if you thought the president hated Jimmy Kimmel Live when it was hosted by Jimmy Kimmel, buckle up, people. Buckle up."

She brilliantly referred to her old nemesis — scratch that — her longtime nemesis Donald Trump as “Mango Mussolini.” She brought the house down.

Then, to me, came the line of the night. O'Donnell described how her child had reacted to the family's move to Ireland, standing up in class to explain the sudden transfer to a new country: "I'm being forced to move to another country because the president of the United States hates my mother. But in all fairness, I believe my mother hates him more."

The crowd erupted. O'Donnell looked dead into the camera and added, "Hi. I know you're watching." And you know he was, and you know he was fuming mad. And you know that perhaps nobody yanks his chain quite like Rosie.

It was vintage Rosie, funny, personal, and aimed with lethal precision at a man who has spent two decades trying to pathetically, cruelly, and crudely knock her down. Well, Rosie’s back, and my money is on Rosie to pick up this fight with Trump, with a vengeance, and win.

The O'Donnell-Trump feud is one of the longest-running grudge matches in American pop culture, dating back to 2006, when she slammed Trump's business bankruptcies during her run on The View.

I was media relations director for Kmart during that period, and Kmart was one of the show’s major sponsors, so I attended many of the show’s live broadcasts. When I saw her up close, I wondered where that “Queen of Nice” nickname came from.

Rosie didn’t hold back with anyone. I would often think to myself how rude she was, and how she could get away with it.

Looking back on it now, well, she’d be the “Queen of Nice” today with all the vulgar rancor. Wow, it was such an innocent time, and it makes me wish now she’d get back on that show full-time (she says she’s going back as a guest) and hammer Trump on a daily basis, because her rudeness toward him is desperately needed.

No offense, Whoopi, but desperate times call for desperate measures. And to that end, it would be great to see Trump desperately try to match her on a daily basis. After all, he has nothing better to do.

He's called her so many things, out of desperation and a lack of ingenuity, including "fat," "disgusting," and "a real loser,” and more recently, he floated the idea of stripping her of her U.S. citizenship after she kept mocking him.

Related: Donald Trump threatens to revoke Rosie O'Donnell's citizenship — but he can't

O'Donnell has never shrunk from the fight. If anything, she leans in harder than almost any other public figure willing to take him on directly, and she did it long before anyone else. We should give Rosie a lot of credit for being a great judge of character since she knew Trump was an a-who long before many of us.

That's precisely what made her Trump's target of choice for so long, but she hit back, publicly, relentlessly, and without flinching.

Eventually, it drove her out of the country. O'Donnell relocated to Ireland, where she's said she found some of the kindest people she's ever met, and, by her own account, a culture that drinks "regardless of who's running their country."

As an Irishman, and a lifelong drinker, I can attest to that!

O’Donnell has spent recent months rebuilding a public life from across the Atlantic: guesting on podcasts, sitting for a candid interview with fellow lesbian Kara Swisher, and talking with Seth Meyers about exactly how hard she planned to pounce on the Mango Mussolini.

Over the last few years, she famously kept a lower profile than she once did, weathered a divorce and plenty of tabloid churn along the way, and came out the other side still standing, still funny, biting, and demonstrating her un-Trump-like ingenuity.

And the timing of her return could not be better.

The American people are becoming exhausted by the Mango Mussolini. Sure, Kimmel, Jimmy Fallon, SNL, and even South Park are all landing solid punches at Trump on a nightly or weekly basis. But none of them has 20 years of personal experience being in the ring with Trump.

O'Donnell has the standing, the scar tissue, and the calluses to take on Trump in a way few others can.

She's earned a reputation over the years for being tough, even mean, when she's stoked. She appears to be finding her footing again, sharpened but not embittered, hilarious without losing the regularness that made her "Queen of Nice" in the first place.

Welcome back, Rosie. You were the first openly gay woman this magazine ever named Person of the Year, and two decades later, you're proving all over again why that title stuck.

So, go ahead, Rosie! Take those gloves off and throw those punches like Ali in his glory days. Oh, and after last night, let’s just say I’ll never look at a mango quite the same way again.

Opinion is dedicated to featuring a wide range of inspiring personal stories and impactful opinions from the LGBTQ+ community and its allies. Visit Advocate.com/submit to learn more about submission guidelines. We welcome your thoughts and feedback on any of our stories. Email us at voices@equalpride.com. Views expressed in Voices stories are those of the guest writers, columnists, and editors, and do not directly represent the views of The Advocate or our parent company, equalpride.