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Anthony Anderson Be Warned! These Are The Cringiest Award Show Hosting Moments

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Sometimes, award show hosts drop the ball. Jo Koy recently joined the ranks of hosts criticized for their awkward award show emceeing after his jokes fell flat at the Golden Globes. He isn’t the first to fumble an award show gig. Anthony Anderson is set to host the upcoming Emmys on January 15. The comedian isn’t planning on “playing it safe,” which may go great or crash and burn. While Anderson has a proven track record hosting the NAACP Image Awards, the Emmys’ choice to have Anderson host is already drawing criticism due to sexual assault allegations. The upcoming Oscars have also opted for a veteran host with Jimmy Kimmel returning for a fourth time. However, just because a celebrity has hosted before doesn’t make them immune to a truly uncomfortable performance.

Hosting is a hard and often thankless job. Many celebrities have delivered cringe-inducing hosting performances. There isn’t a trophy for “worst award show host of all time,” but if there were, the nominees are…

David Letterman at the 1995 Oscars

While many hosts on this list aren’t know for their comedy chops, David Letterman had already hosted 11 seasons of Late Night when he emceed the 1995 Academy Awards. However, his skills didn’t translate for the event. His opening monologue included a joke about celebrities who had supposedly similar names. In it, he says, “Oprah. Uma. Oprah. Uma. Oprah. Uma. Have you kids met Keanu?” to an almost silent crowd, and multiple jokes later in the show are received the same way.

Letterman has proved his influence as a comedian and a host in the late-night talk show space, but this performance was a big misstep.

No Hosts at the Oscars

The Oscars have taken some risks when it comes to out-of-the-box choices. In 1958, an animated Donald Duck even served as a host—however, the decision to forgo hosts entirely made for a couple of less-than-memorable years. The Oscars went without a host in 2019-2021, but this wasn’t the first time.

The 61st Academy Awards in 1989 also had no host. While more recent host-less Oscars have been fine, if not lacking a little sparkle, the 1989 awards were a noted awkward mess complete with a panned opening number.

Chelsea Handler at the 2010 MTV Video Music Awards

Chelsea Handler has hosted TV shows and specials and is even emceeing the 2024 Critics Choice Awards. However, the 2010 VMAs didn’t go well for her. During the opening number, Handler came down on a platform with a doll house on her head to Lady Gaga’s Bad Romance and was swarmed by a mob of dancers. She then released a dove from under her skirt. Instead of flying away, the dove landed on a dancer that audibly said, “Oh sh*t.” This sets the tone of the messiness that plagued this performance. Between yelling and some racist jokes that did not land, this performance didn’t deliver on laughs or gravitas.

Jerry Lewis at the 1959 Oscars

The issues during the 1959 Academy Awards weren’t really comedian Jerry Lewis’s fault. The show ran 20 minutes short, and Lewis tried to fill time by ad-libbing and having the orchestra play “There’s No Business Like Show Business.” Lewis wasn’t the only host of the ceremony. He was joined by Mort Sahl, Tony Randall, Bob Hope, David Niven and Laurence Olivier. However, he was the one who was left in the lurch by the run time issue and is remembered for the snafu.

Tom Bergeron, Jeff Probst, Heidi Klum, Howie Mandel, and Ryan Seacrest at the 2008 Emmys

Having seasoned reality show hosts emcee the Emmys might sound like a good idea, but in practice, it didn’t land. The choice to have the five nominees for the then-newly-announced Best Reality Host category didn’t pay off. The hosts of Dancing with the Stars, Survivor, Project Runway, Deal or No Deal, and American Idol struggled through this gig. There may have been too many hosts, but the real issue was the performance was seemingly unscripted.

Chevy Chase at the 1988 Oscars

The 1988 Oscars were Chevy Chase’s second time hosting. While his job at the 1987 Oscars wasn’t memorably fantastic, it was good enough to have him invited back in 1988 to host again. However, when Chase opened the show with “Good evening, Hollywood phonies,” he lost many in the audience. The show took place during a WGA strike, and it showed. While he got some good laughs early on, many of the monologue jokes fell flat, and Chase’s ad-libs didn’t help.

James Franco and Anne Hathaway at the 2011 Academy Awards

James Franco and Anne Hathaway weren’t the obvious pair to host together, but the academy had seen success pairing up Alec Baldwin and Steve Martin host together the year before. Franco and Hathaway, unfortunately, had no chemistry. While Hathaway tried to keep the energy up, the lackluster jokes and Franco’s low-key delivery made this performance bomb. Due to the painfully awkward host segments, the 2011 Oscars are remembered as one of the worst, if not the worst, ever.


Award shows are hard to host and are often fraught with awkward moments. Many of these poor performances were one-time missteps in much longer hosting careers. Others haven’t tried hosting again. However, either way, they are remembered by some truly cringe award show moments. Hopefully, the upcoming Emmys, Oscars, Anthony Anderson, and Jimmy Kimmel stay far away from this list.

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