How to Bet on Oscar Host & Performer Lineups: Host Shortlist, Presenter Pairings & Medley Odds 2026

The Academy has officially confirmed the news that Hollywood has been buzzing about: Conan O’Brien is returning to host the 98th Academy Awards! Following his universally praised performance at the 97th Oscars, the decision to bring him back was an easy one for producers. This confirmation shifts the focus for celebrity fans and casual bettors. The question is no longer who will host, but how Conan will top his triumphant first outing. With the ceremony set for March 15, 2026, let’s dive into the exciting new prop bets that have opened up now that our host is locked in.

Why Conan’s Return Was a Sure Bet

Conan didn’t just host the last Oscars; he revitalized them. The broadcast drew an impressive 19.69 million viewers, making it the most-watched ceremony in five years. Beyond the ratings, the show dominated social media with over 104 million interactions. Academy CEO Bill Kramer and President Janet Yang praised Conan as the “perfect host,” celebrating his ability to guide the evening with “humor, warmth and reverence.” This track record makes betting on the specifics of his performance all the more interesting, as he and returning producers Raj Kapoor and Katy Mullan will be looking to replicate that incredible success.

Betting on the Opening Jokes

Conan’s opening monologue is guaranteed to be a highlight, and it’s a goldmine for prop bets. In his official statement, he cheekily said, “The only reason I’m hosting the Oscars next year is that I want to hear Adrien Brody finish his speech,” referencing the actor’s record-breaking long speech at the previous ceremony. This gives us our first major betting category: Will Adrien Brody make a cameo during the monologue? Other fun wagers include predicting the over/under on jokes about his own height, the odds of an Andy Richter appearance, and which of his famous friends will be the first to get a gentle roast.

Who Joins Conan on Stage?

While Conan is the solo host, the show is always filled with planned bits and surprise guests. This is where you can make some clever wagers. With his popular podcast “Conan O’Brien Needs a Friend,” the pool of potential guest stars who have great chemistry with him is enormous. Will a beloved former guest join him for a sketch? You could also bet on a segment inspired by his travel series, “Conan O’Brien Must Go.” The producers are known for creating a “visually stunning show,” so expect some elaborate, pre-taped segments. A long-shot bet could even be on a cameo from the cast of his upcoming film, “If I Had Legs I’d Kick You.”

Predicting Presenter Pairings

The host’s tone often influences the presenter pairings, and with Conan’s comedic and affable style, expect to see some fun and unexpected duos. The returning producers will likely lean into pairings that create viral moments. As you look at the big films of 2025, you can start making educated guesses. There are several major upcoming films, creating instant betting opportunities. For instance, what are the odds that the stars of the two competing Frankenstein movies, Oscar Isaac and Jacob Elordi (“Frankenstein”) and Jessie Buckley and Christian Bale (“The Bride”), will be paired up? Or that the leads of the musical sequel “Wicked: For Good” will present together?

Musical Moments and Medley Odds

The Best Original Song performances are always a spectacle, and the betting doesn’t stop at who will win. You can place wagers on the specifics of each performance. Will a pop superstar bring out a surprise musical guest? Will a nominee opt for a stripped-down acoustic performance versus a full-blown stage production? Another classic wager is on the “In Memoriam” segment. Predicting which artist will be chosen to perform the tribute song is a popular, if somber, bet each year. With Conan’s deep love for music, his introductions to these moments are sure to be especially thoughtful.

The Three-Peat: Odds on a 2027 Return

Conan has already cleared the first hurdle: he was successful enough to be invited back. Now, the big-money question is whether he can deliver a second time and secure a hosting three-peat for the 99th Oscars in 2027. This is the ultimate future bet. If he once again delivers a critically acclaimed show with strong ratings, the odds of him returning will be extremely high, making him a heavy favorite. However, if viewership dips or the sophomore effort doesn’t capture the same magic, the odds will swing dramatically, making a “no” bet much more valuable. His 2026 performance is essentially an audition for 2027.

With Conan O’Brien’s return, the 2026 Oscars promise to be an evening of sharp comedy and genuine warmth. His confirmed presence allows fans to move past the hosting speculation and focus on the delightful details of the show itself. From betting on his monologue jokes to predicting a potential third hosting gig, these wagers add a fantastic layer of interactive fun to Hollywood’s biggest night. The stage is set for another memorable ceremony, and the betting possibilities are more exciting than ever.