Conan O’Brien returns to Hollywood’s Dolby Theatre on Sunday to host the Academy Awards for the second consecutive year. The beloved comedian earned rave reviews for his 2025 debut, and expectations are high for an encore performance. If anyone can keep Hollywood’s biggest night running smoothly, it’s O’Brien.
Past ceremonies, however, have proven that hosting the Oscars is one of the toughest gigs in showbiz. For every memorable triumph, there’s been an equally unforgettable misfire. As fans get ready to tune in on ABC, we’re looking back at the hosting moments that didn’t quite land—ranked from mildly awkward to absolutely unforgettable.
As fans get ready to tune in for Hollywood’s biggest night, Parade ranks the worst-ever Oscars hosts—from least to most disastrous!
10. Steve Martin and Alec Baldwin’s Co-Hosting Chemistry Fell Flat
Both Martin and Baldwin are hilarious on their own—and had already proven their chemistry in the 2009 comedy It’s Complicated. But as co-hosts of the 82nd Academy Awards in 2010, something just didn’t click. Viewers noticed awkward pauses and a shaky rhythm between the two, starting with a splashy showgirl entrance that simply set the wrong tone. Some of their jokes landed poorly—including a racially charged callback to Martin’s 1979 comedy The Jerk—and a quip from Baldwin implying Woody Harrelsonhad smoked weed before the show.
Martin, who had far better solo outings hosting in 2001 and 2003, has since said he’s done with the gig. “It’s a lot of work,” he told the LA Times in 2024.
9. James Franco and Anne Hathaway Couldn’t Find Their Rhythm
Pairing two of Hollywood’s most popular young stars seemed like a smart play to attract younger viewers to the 83rd Academy Awards on February 27, 2011. Instead, Franco and Hathaway turned in one of the most mismatched co-hosting performances in Oscar history. Hathaway brought boundless energy while Franco seemed checked out, leaving her visibly stranded onstage. The two never found a groove, and the whole evening felt off-balance.
Hathaway, at least, got a much happier Oscar memory two years later when she won Best Supporting Actress for Les Misérables.
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8. Neil Patrick Harris’ Oscar Night Didn’t Go as Planned
Neil Patrick Harriswas riding high from the success of How I Met Your Mother when he took the stage to host the 87th Academy Awards on February 22, 2015. But several moments throughout the evening drew criticism. A joke about documentary producer Dana Perry’s dress—made just after she emotionally dedicated her award to her late son—struck many viewers as poorly timed. And a running bit involving Octavia Spencer guarding a locked box of envelopes also rubbed audiences the wrong way—as did a joke about Selma star David Oyelowo’s accent.
Harris later took it in stride, telling Variety that hosting the Oscars is simply “a beast.”
7. Chevy Chase’s Solo Oscar Hosting Didn’t Land
Chase earned a solo hosting spot at the 60th Academy Awards on April 11, 1988—after a well-received turn co-hosting the previous year with Goldie Hawn and Paul Hogan. But on his own, the evening fell apart quickly. He opened by saying, “Good evening, Hollywood phonies.” The line landed with a thud—offending a room full of the people he should have been entertaining.
In fairness, Chase was working with limited material. A Writers Guild of America strike began shortly before the ceremony, which left him without the usual stable of writers—and it showed. His riffs on Teamsters and film critics never found their footing, and what should have been a victory lap turned into a rough night.
6. Bob Hope and Company Stumbled Into a Political Firestorm
The April 8, 1975 ceremony featured a powerhouse multi-host lineup: Bob Hope (who hosted a record 19 times), Frank Sinatra, Sammy Davis Jr. and Shirley MacLaine. But the evening took a sharp turn when Best Documentary Feature winner Bert Schneider read a telegram from the Viet Cong thanking the American anti-war movement during his acceptance speech for Hearts and Minds.
Hope reportedly urged Sinatra to read a disclaimer later in the broadcast stating that the Academy was not responsible for political statements made during the show. The move infuriated MacLaine, who reportedly confronted Sinatra backstage. With a new generation of filmmakers reshaping Hollywood in the 1970s, the moment exposed a growing divide—and left Hope and Sinatra looking out of step with the times.
5. Jerry Lewis Had to Fill 20 Minutes of Dead Air
Most Oscar ceremonies run long—but the 1959 show had the opposite problem. Jerry Lewis was the last in a rotation of six hosts—alongside Mort Sahl, Tony Randall, Bob Hope, David Niven and Laurence Olivier—and when the final award was presented a full 20 minutes ahead of schedule, it became Lewis’ responsibility to fill that gap on live television.
What followed could best be described as pure chaos. Lewis encouraged the orchestra to play multiple reprises of “There’s No Business Like Show Business,” while Golden Age stars paired off and danced onstage. His former comedy partner Dean Martin grabbed an extra Oscar as a gag. Lewis conducted the orchestra, attempted to play a trumpet and generally scrambled to keep the show alive—until NBC mercifully cut to a short film to run out the clock.
As Slash Film has noted, most Academy Awards ceremonies run too long, but incredibly, as part of a group of hosts in 1959, Jerry Lewis had to ad-lib at the end to fill time! Lewis, as the last man up of in a rotation of six hosts (that included Mort Sahl, Tony Randall, Bob Hope, David Niven and Laurence Olivier), found out the final award was presented 20 minutes ahead of the TV schedule.

4. Chris Rock’s Irreverence Crossed a Line
Chris Rock was purposely brought in to host the 77th Academy Awards on February 27, 2005 in order to be edgy and attract younger viewers. But his set veered from irreverent to mean-spirited—particularly a lengthy riff mocking Jude Law’s prolific output—essentially dismissing him as a lesser version of Tom Cruise. The bit went on long enough to make the room visibly uncomfortable.
USA Today critic Robert Bianco called Rock’s performance “loud, snide, and dismissive.” To his credit, Rock proved he could rise to the occasion when he returned to host in 2016, navigating the #OscarsSoWhite controversy with sharp, thoughtful comedy.
3. David Letterman’s ‘Oprah-Uma’ Became an Oscar Punchline—Just Not the One He Wanted
David Letterman hosted the 67th Academy Awards on March 27, 1995 and delivered what many consider the most infamous flop of a joke in Oscar history. During his opening monologue, he introducedOprah Winfreyand Uma Thurman to each other from the stage by saying, “Oprah, Uma. Uma, Oprah.” For reasons still unbeknownst to us, he kept returning to the bit throughout the night—except it never caught on with the audience.
Letterman himself has been refreshingly honest about how it went. He told The Hollywood Reporter in 2020 that even before the show, he sensed trouble—and that the whole evening became a self-fulfilling prophecy.

In 2020, Letterman told THR that his Oscars gig was “an explosion of excrement.” The comedian admitted after he’d accepted the spot, he felt the foreboding of disaster. “I had an awareness that, ‘Oh, by the way, this isn’t going to go well.’ And it became a self-fulfilling prophecy.”
2. The Infamous No-Host Snow White Number
As it turns out, having no host at all can be just as disastrous as having a bad one. The 61st Academy Awards in 1989—produced by Allan Carr—are widely considered the most cringe-worthy in Oscar history. Believe it or not, it started from the very first moment—instead of an opening monologue, actress Eileen Bowman took the stage as Snow White in an elaborate musical number that included Merv Griffin singing “I’ve Got a Bunch of Lovely Coconuts” and a duet of “Proud Mary” with Rob Lowe. And no, this was not a fever dream.
The reaction was swift. Audience members—including some of Hollywood’s biggest names —sat in visible disbelief. In fact, Disney sued the Academy for unauthorized use of the Snow White character! They ultimately dropped the lawsuit after receiving a formal apology and signed an agreement stating that Disney characters wouldn’t be used without permission in the future.
1. Seth MacFarlane’s Oscar Night Crossed Every Line
Seth MacFarlane hosted the 85th Academy Awards on February 24, 2013, and delivered a performance that has only aged worse with time. The Family Guy creator opened with a musical number called “We Saw Your Boobs,” singling out actresses by name—many of whom were sitting in the audience—and some of whom appeared in scenes that depicted sexual assault. The number drew immediate backlash and remains one of the most widely criticized moments in Oscar history.
MacFarlane also made a joke referencing Scarlett Johansson’s private photos that had been leaked online without her consent, and turned a description of Django Unchained into a punchline about Chris Brown’s assault ofRihanna. What was framed as edgy comedy read as something far worse—a host using Hollywood’s biggest stage to demean women and make light of violence against them.
It’s no surprise the moment is frequently cited as a turning point in how audiences judge award show humor. As The Guardian put it at the time: What was he thinking?
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