Intro for November 3, 2026
– 3 min read
Dear Gossips,
A couple of interesting Matt Damon sightings this week – more notable than usual because Matt Damon, when he isn’t on an active press tour, doesn’t really do the circuit. But he is one of the frontrunners for the Best Actor Oscar this season, the lead and title character in the film that will be contending for the most nominations and is considered a heavyweight for Best Picture. Right now it’s a three-way race between Matt, John Malkovich, and Andrew Scott.
Matt made a surprise cameo on the latest episode of The Gilded Age alongside David Letterman. This, apparently, will also be part of Matt’s appearance on the new season of Letterman’s My Next Guest Needs No Introduction, reportedly set to premiere before the end of the year. (The episode I’m most looking forward to is Julia Roberts – the kids don’t know but the olds remember how famously flirty they were over the years on The Late Show.) Not that Matt Damon would ever turn down an invitation from David Letterman, for Matt, the Letterman timing is also perfect. Academy voters can watch him through the holidays and into the new year making his case alongside an interviewing legend who is also a legendary comic … and, of course, so much more known among the Oscar old guard than, say, the YouTube chicken shows.
Being on a talk show is one thing, a standard stop on an Oscar campaign, but could you have predicted that Matt Damon would also pop up at a fashion event? His attendance at the CFDA Fashion Awards last night was motivated by more than an Oscar nomination. Matt was there with his second-eldest daughter, Isabella, who just a couple of months ago signed with IMG Models. And Matt Damon answering questions on a fashion red carpet, looking pretty sharp in Ralph Lauren? Also unusual.
Or maybe, in this timeline, not that unusual. We are, after all, in the age of Gen X celebrities and their model offspring – Matt Damon is hardly the first. There’s Nicole Kidman’s daughter, Sunday. And Apple by Gwyneth Paltrow and Chris Martin; Iris of Jude Law and Sadie Frost; Naomi Watt’s and Liev Schreiber’s child Kai… just to name a few. They are all over the runways. So far Isabella has not walked during a fashion week, at least not that I can remember, but she was recently featured in a J.Crew campaign so it’s probably only a matter of time.
Isabella is now 20 years old. Violet Affleck is also 20 years old. Twenty years ago, if you had to predict, between Matt Damon and Ben Affleck, whose children would be the model nepo babies and whose would go to Yale, which one would you have said?
Yours in gossip,
Lainey
Isabella Damon and Matt Damon attend the 2026 CFDA Fashion Awards, November 2, 2026
