Ed Sheeran showed up wearing a red dress on 'Jimmy Kimmel Live'— and instantly regretted it
Ed Sheeran made a hilarious appearance on 'Jimmy Kimmel Live!' where he dressed up as a beloved character from the Broadway musical, Annie. Jimmy Kimmel, known for his comedy gimmicks, has made a career out of making fun of celebrities. According to E! News, during a Halloween episode, Kimmel once made Mindy Kaling dress up as Captain Hook on his late-night show while he dressed up as Snow White. There is no surprise; only he could have thought of Ed Sheeran as Annie.
The show commenced, and Kimmel broke the news that NBC was planning a live televised production of Peter Pan. Kimmel quipped, "We will be hearing a live production of the musical Peter Pan... what's interesting about that is Peter Pan will be played by the very talented Allison Williams, who is a woman. She is on the HBO show 'Girls.'" He then humorously added, "That's great, but tonight I have the honor of announcing that my network, ABC, has decided to top them." Building up the anticipation, Kimmel continued, "On November 3, we will be hearing a live production of the musical Annie, and here tonight to give us a sneak preview, the actor who will be playing the lead role of little orphan Annie... Mr. Ed Sheeran!"
As the audience erupted in laughter, Sheeran walked onto the stage, donning Annie's iconic red dress, complete with a white collar and belt. He was accompanied by a stuffed dog on a skateboard and Annie's loyal companion, Sandy. Kimmel couldn't help but joke, "Annie is furrier than Sandy, it turns out!" Attempting to stay in character, Sheeran began singing one of his classic songs, 'Daaaaaa...' he started, soon realizing the awkwardness of it; he quickly broke character, exclaiming, "Jimm...Jimmy, I can't f**king do this, man. I'm sorry." He then exited the stage, dragging the stuffed dog behind him, leaving both Kimmel and the audience in fits of laughter. This appearance of Sheeran on 'Jimmy Kimmel Live!' showcased his jolly and playful side.
However, this is not the first time Sheeran showcased his humorous side on TV. According to an Express & Star article, during one of his appearances with James Corden, Sheeran took on a hilarious challenge on Carpool Karaoke, where he stuffed his mouth with Maltesers while singing. Corden gave up after 26, spitting them out onto the street, but Sheeran kept going, managing an impressive 55, declaring a glorious win. The 'Shape of You' singer also displayed his acting chops, proving that his talents extend far beyond music. According to Screen Rant, fans fondly remember his 'Game of Thrones' cameo, where he played a singing Lannister soldier. Sheeran, then 26, was dressed as a soldier and sang around a campfire when he caught the attention of Maisie Williams, AKA Arya Stark, as she rode through a forest on horseback. Stark said to Sheeran's unnamed character, "It's a pretty song; I've never heard it before." Sheeran replied, "It's a new one."