Rosie O’Donnell: A Late Night Show Would Be Perfect for Trump’s Rival

Late night is in the doldrums. It’s not just that the remaining hosts are taking much of the summer off. But, post-Stephen Colbert on CBS, ABC’s Jimmy Kimmel and NBC’s Jimmy Fallon both feel closer to the end of their respective tenures than the beginning. The whole genre feels ripe for a shake-up — lest it go away entirely.

Enter Rosie O’Donnell. The comedian and Donald Trump antagonist just spent a week filling in for Jimmy Kimmel, and the results were TV magic. Over four nights, O’Donnell, the 1990s talk show host whose two stints on “The View” both fizzled out, proved that she may yet have another act, and it may be on one of television’s grandest — diminished, but still grandest — stages.

Yes, O’Donnell skewered President Trump, and it, of course, drew attention: O’Donnell is, these days, perhaps best known as an object of Trump’s obsession. (Indeed, the White House issued a statement that O’Donnell “is a nasty woman and a total slob whose brain has been completely destroyed by Trump Derangement Syndrome.”) But her approach to her monologues tended toward reconnecting with the audience over rat-a-tat resistance patter. Combining this impulse for empathetic opening-up with a savage instinct for finding the laugh, O’Donnell proved that, while late night may be growing a bit soft, she arrived at “Kimmel” ready for the spotlight. 

It’s been almost 40 years since Joan Rivers tried to break into the late-night boys’ club — and got fired by Fox after a single season. O’Donnell’s hiring as a woman at a flagship late-night show would break further ground — but would also bring in someone who totally reveres television and knows how to make it well. A form of TV that seems close to dying could use a jolt of energy, and O’Donnell, with her built-in fanbase and her ability to connect with, and provoke, audiences, might just be late night’s future. 

Sound familiar? That’s because we just saw it play out in fiction. In the universe of “Hacks,” women have been given only paltry chances to claim their piece of late night. Eventually, Jean Smart’s character Deborah Vance, whose comedy alternately undermines and exalts her own image and is rooted in her rock-solid showbiz chops, gets her chance. (Let’s, for now, not worry about the fact that it all blows up in relatively short order.) 

On “Hacks,” as in our world, late-night looks like a glass cliff for women — the field is shrinking, with CBS now out of the game entirely, just in time for a woman to potentially get called up. And yet, O’Donnell didn’t seem to mind, and hit the ground running on “Kimmel.” The female late-night hosts of recent vintage, CBS’ Taylor Tomlinson and NBC’s Lilly Singh, have seemed limited by both buried-in-the-evening time slot and by relatively low name recognition. O’Donnell’s hiring would be a moment that would electrify late night, drawing in an underserved audience of women and gay men and generating reams of press. 

Shifting from wish-casting O’Donnell into a late-night berth and actually considering what might be possible, there are obvious counterarguments. After early success, O’Donnell has suffered disappointment after disappointment. She left “The View” in 2007 over an incident in which she and co-host Elisabeth Hasselbeck were presented arguing in split-screen, and then returned for another short run, from 2014 to 2015, that was simply unremarkable before she once again quit. In between, she tried an Oprah Winfrey Network talk show and a Sirius radio show. Nothing stuck. 

But unlike on “The View,” where she was one of several panelists sniping round-robin style, O’Donnell, here, would be in a position that we know suits her — behind a desk, telling jokes. She came into “The View” to blow it up; as regards TV talk, though, we already know she’s a traditionalist. In childhood, O’Donnell was a student of early TV, and she seems to have totally internalized old-school broadcast rhythms. Among them are a total and complete interest in whoever is in front of her. I’ve written before that, in his final months, Colbert seemed to come most alive when his interview subjects got around to praising him, and Kimmel or Fallon’s strengths are not necessarily in interviewing, either. O’Donnell, on the other hand, knew how to steer guests from the digressive Smart to the antsy Richard Gadd toward the funniest and most charming versions of themselves. 

She was coming to the show with the zeal of someone who’s been out of the game too long and eager for her at-bat. The standard monologue nowadays can feel like a laundry list of cracks about Trump’s daily misdeeds. O’Donnell’s curiosity — for all that she’s the President’s bête noire — ranged more widely. She got personal about her family and dating life in a manner I’d never expect a Jimmy to do. And she did so with a sense of real craft, the sort that comes when you’re excited to be somewhere and not just clocking in for season umpteen. 

But then, O’Donnell is, first, a storyteller, well acquainted by now with fitting the tales she tells within the time between the “Applause” sign lighting up and the first commercial break. The discursive looseness of her posting on social media — where, for instance, she recently disclosed her face-lift — falls away when the camera is on her. When I interviewed her last year, about her guest role on “And Just Like That,” she described to me that, in her newly adopted home of Ireland, the local pharmacist was so kind to her that O’Donnell developed a crush. On her first Kimmel monologue, the story was blown out, underlined, illuminated by a star’s charisma. Of course, it built to the perfect punchline.

Who knows if she’d get the chance — Kimmel perennially makes noise about wanting to leave, but hasn’t yet — or if she’d want to. (Although the fact of her returning to the U.S. before the end of the Trump presidency, which she once swore she wouldn’t, suggests a bit of fire in the belly.) But one wonders if the industry, not just viewers, shares the sense that the TV landscape is significantly more interesting with O’Donnell in it — and that interest is exactly what late-night is lacking. If this is O’Donnell’s moment, it’s not because of who the President is. It’s because of who, over four remarkable nights of old-school television, she reminded us she is.