Intro for May 13, 2026

Dear Gossips,

The Oscar Academy confirmed yesterday that Conan O’Brien will return to host the Oscars next year, for the third year in a row. And I’m pretty sure nobody is mad about this. This, as people have been saying for years, is a thankless job (that doesn’t pay much, if anything, at least in the immediate). In the years preceding Conan taking over the job, the Oscar host couldn’t win, especially as more and more people started watching and chirping on social media. Also, Conan doesn’t need the job – he has more than enough jobs now to keep him busy, and more than enough opportunities being offered to him with the success of his other jobs and with how well he’s hosted the Oscars…

Obviously, then, if Conan’s coming back to make it a three-peat, it must mean he enjoys it on some level, that he likes the rush of it, and the creative push he and his team get from it.

What’s interesting about Conan locking in for the Oscars in 2027 is that it sets up an intriguing situation for the year after. The 99^th Oscars will take place on March 14, 2027 followed by the 100^th anniversary of the event on March 5, 2028, which will be the last year that they will air on ABC. From there, the Oscars will move to streaming on YouTube in 2029, kicking off a new century of Hollywood’s most prestigious award show.

For the Academy, the 100^th anniversary edition of the Oscars will be a huge deal – so they’ll be coming off three years in a row with Conan presiding over the ceremony and, presumably, it’d be a pretty big risk to take, asking someone else to come in for the 100^th after three years of familiarity with Conan. They’ll want to make the 100^th Oscars as big of a deal as possible, they’ll do whatever they can to ensure it’s a slam dunk, one for the books. Is it possible, then, that Conan will be involved, in some way, for the 100^th Oscars? Perhaps a multiple host scenario bringing back a few previous hosts along with him? That’s a lot of hosts though, would that be too much to manage? And what would the fallout be for hosts who aren’t invited back? (James Franco can stay seated, nobody will miss him.)

These questions, for some, might be a headache but as someone who works in television, who has worked with so many brilliant producers, the hypotheticals at this point are fun thought experiments. I would f-cking LOVE to be part of the team mulling over this future – and it’s not that far away, they aren’t thinking about it every day but I guarantee you they’ve thought about it a little, that there’s been at least a couple of look-ahead conversations. Or, you know, by then maybe they’ll just AI a host and call it a day.

Yours in gossip,

Lainey