Our 2024 ‘The Wedding Singer’ Dream Reboot Cast

Every time of year is the best time to rewatch The Wedding Singer, the 1998 film that turned Adam Sandler into the ideal romantic lead. As Robbie Hart, he woos Drew Barrymore’s Julia despite her engagement to another man (who turns out to be as evil as he seems — a philanderer who doesn’t value his fiancée at all). Regardless, the movie stands the test of time as one of our favorite rom-coms with iconic tunes, unforgettable jokes, and the charming chemistry that resulted in a trilogy of Adam and Drew-led romantic comedies.

Almost 30 years later and in the height of nostalgic reboots, it’s time for The Wedding Singer to get its chance in the spotlight once again. It was transformed into a musical in 2006 starring musical comedian Stephen Lynch and Broadway darling Laura Benanti, but in 2024, we’re now asking the reboot gods not to overlook The Wedding Singer. So we’ve decided to make it easy for them by sharing our dream reboot cast.

Robbie Hart — Bo Burnham

Before becoming a leading rom-com man, Adam Sandler was a goofy musical comedian, which sets the precedent for whoever plays Robbie. While Bo is *slightly* older than Adam was when he originated the role, he’s definitely still young enough to play the part. Not only is his comedic timing on point and are his musical talents ideal, but Bo could bring a new poignancy to the role through his recurring theme of existentialism. Of today’s leading men, there’s no better person than Bo Burnham to fill Adam’s shoes.

Julia Sullivan — Dakota Fanning

Hear us out — we know that Dakota Fanning was once a big-time Hollywood child star. But you know who else first made it big as a child? None other than Drew Barrymore, who got her big break in E.T. when she was only 6 years old. Both Dakota and Drew were America’s sweethearts at one point, and the character of Julia necessitates a sort of predetermined empathy. Her hopeless romantic naivete make us both root for her and feel ashamed at the same time. While Dakota hasn’t been a major rom-com star yet, this could be her foray from child star to indie actress to rom-com leading lady.

Holly Sullivan — Awkwafina

While Julia and Holly are supposed to be cousins in the original Wedding Singer, various iterations haven’t specified their relationship. All that matters is that they are close friends and that Holly is a little more experienced. But Holly is also the funny, charismatic, charming, and outgoing friend to Julia, all qualities that Awkwafina has. She would bring her much-needed high energy to the role, providing a fun bit of comedic relief for the central love story while bringing her own twist to a truly modern 2024 woman.

Sammy — Jerrod Carmichael

Arguably a man with leading love interest energy, Jerrod Carmichael would be THE pick to play Bo Burnham’s on-screen bestie. The two are behind-the-scenes collaborators, with Bo directing two of Jerrod’s comedy specials, 8 (2017) and Rothaniel (2022). While Sammy is a bit of a womanizer in the original Wedding Singer, Sammy could be more of a man’s man in an updated 2024 version of the film. Between Jerrod’s comedic timing and pre-existing chemistry with Bo Burnham, there’s no better pick to play his partner-in-crime.

Glenn Guglia — Theo James

After playing the philandering Cameron in White Lotus, Theo James is the guy to play a cheating fiancé. He has the charisma and good looks that explain why Julia would be with him in the first place, despite a minor age gap and seemingly clashing personalities. Glenn is easily the most hateable character in The Wedding Singer and after seeing how Theo can so easily play a wealthy “bro,” he could easily take on the role in the classic rom-com.

Linda — Juno Temple

The Ted Lasso and Fargo star Juno Temple can be both sweet and spicy, which makes the perfect Linda. Originally played by model Angela Featherstone, Linda had the starpower of a supermodel behind her. Although Juno wasn’t a supermodel herself, her most well-known character, Keeley, was both a model and influencer, so seeing her on our screens evokes much of the same feeling we got from watching Angela. While Juno would perhaps bring a bit more empathy to the role, we know she can play a cold-hearted boss girl when she needs to, and we can totally imagine her finding a way to manipulate Bo’s Robbie.

George — Patti Harrison

George is a character who defies gender and whose most important facet of their personality is their queerness. Originally played by Alexis Arquette, who is trans, we wanted to cast the role with someone just as hilarious to keep up with the modern day. Patti is a trans woman, but beyond that, she’s a comedic gem. With comedy specials that include musical comedy, an infectious stage presence, and an absurdity that could be compared to George’s, she is the ideal actor to take over the iconic role as the backup singer. Although perhaps in a 2024 version, Patti will have an obsession with someone slightly more relevant than Boy George, giving her character a different name as well.