The annual Academy Awards can offer a fascinating glimpse into what’s dominating popular culture. The nominees across so many categories, not just Best Picture, show us what resonates with the diverse Oscar voters, and sometimes there are happy accidents along the way. March 15 heralds the 98th Academy Awards, hosted by beloved returning favorite Conan O’Brien. His hosting job last year suggests we’re in for another rollicking ride, but this time, there’s a fun little twist. O’Brien has some skin in the game, having appeared in the phenomenal If I Had Legs, I’d Kick You, with Best Actress nominee Rose Byrne. O’Brien is thus in a strange little mini-echelon of Oscars hosts, who emcee the show in the year in which a film of theirs is nominated.
Technically, O’Brien is not nominated, though he is effectively low-key in If I Had Legs, I’d Kick You as Byrne’s character’s therapist (and colleague) who also can’t stand her. But by being in an Oscar-nominated film (for which Byrne has a decent chance of winning, even with Jessie Buckley racking up hosannas for Hamnet), O’Brien joins a weird little fraternity. Just six past Oscars hosts oversaw the proceedings when they, themselves, were nominated, and looking at that list is a veritable Who’s Who of “…Wait, they hosted the Oscars?”
In 1959, David Niven became the only Oscars host to win the same year he emceed, taking home the gold for Best Actor in Separate Tables. (He was, to be fair, one of six co-hosts that year, with Bob Hope, Mort Sahl, Jerry Lewis, Laurence Olivier, and Tony Randall.) Niven, an excellent and eminently British actor, is famously the source of an even more memorable bit of Oscar trivia, inadvertently sharing the stage with a streaker in the mid-1970s, leading to one of the great improvised one-liners in the history of live TV.
Three of the other five nominated hosts all were up for Best Actor, though they all came away empty-handed. In 1973, Michael Caine was nominated for his work in Sleuth, and co-hosted with Carol Burnett, Rock Hudson, and Charlton Heston (the original Fab Four, don’tcha know). As was the case with Niven, Caine’s hosting gig and nomination that year paled in comparison to another memorable moment: Caine losing out to Marlon Brando in The Godfather, leading to a controversial acceptance speech on his behalf by Sacheen Littlefeather.
Three years later, Walter Matthau wasn’t just a Best Actor nominee for The Sunshine Boys. He was an Oscars co-host along with Robert Shaw, George Segal, Goldie Hawn, and Gene Kelly. Matthau’s co-star, George Burns, won Best Supporting Actor for the same film. Matthau, like Caine, never stood a chance in his category, losing out to Jack Nicholson in One Flew Over the Cuckoo’s Nest. (This was the same year that the Milos Forman film became the second of all time to win for Best Picture, Director, Actor, Actress, and Screenplay, after It Happened One Night and before The Silence of the Lambs.)

Hawn would crop up again as co-host the same year as both Chevy Chase and one of the more dated Oscar nominees of all time, Paul Hogan. See, kids, there was once a time when all you had to do was write a fish-out-of-water comedy about a very Australian man spending time in the United States, and get an Oscar nod out of it. Yes, Hogan got a Best Original Screenplay nomination for Crocodile Dundee in 1986. While that year’s Best Picture winner, Oliver Stone’s brilliant and harrowing Vietnam War film Platoon was nominated in the same category, it was Woody Allen who won for Hannah and Her Sisters. (In a fun coincidence, Caine won that year for the same film, in the Best Supporting Actor category.)
Most recently, two extremely different hosts got nominated. It never really made any sense why James Franco was hosting the Oscars with Anne Hathaway, or, y’know, at all. It did make sense that he would be nominated for his intense work in Danny Boyle’s 127 Hours, though he lost Best Actor to Colin Firth for The King’s Speech. It barely made any sense why Seth MacFarlane was hosting the Oscars two years later, or why he got a Best Original Song nomination for the obnoxiously raucous summer comedy Ted, for “Everybody Needs a Best Friend.” Like a few other hosts listed here, though, he never stood a chance against eventual winner Adele for the eponymous song in Skyfall.
So if nothing else, Conan O’Brien is hanging out with a strange coterie of past Oscars hosts. His presence in If I Had Legs, I’d Kick You occupies the opposite of many examples above. It didn’t make much sense why they hosted, but it often was very logical that and why they got nominated. O’Brien has spoken about how he had to be convinced to appear as a non-comic character in the Mary Bronstein film, but it does work in the end. Even if his excellent co-star doesn’t win an Oscar, O’Brien will almost certainly have two years in a row of being a hilarious and brilliant Oscars host, which is, frankly, more than you can say for the others in this unique sub-category of hosts/nominees.
