With A Real Pain a hit, Jesse Eisenberg is set to direct a musical, but the genre has been the ruin of many a director before him.

Making a big-budget musical seems to be the great white whale for any aspiring director. Many have tried, many have failed. Those include names like Martin Scorsese, Francis Ford Coppola, and most recently Todd Phillips. Undeterred, Jesse Eisenberg, fresh off the success of his breakout hit A Real Pain, has signed on to direct his third movie which – wait for it – is set to be a musical comedy.

Indeed, according to Deadline, Julianne Moore and Paul Giamatti are set to co-star in the film which, is about “a shy woman who is unexpectedly cast in a local production of an original musical. Under the spell of the strong-willed and enigmatic director, she loses herself in the role and the high-stakes world of this community theater production.”

Sounds good, right? Given how A Real Pain is, it may well be, but, the non-musical/musical genre has humbled some truly great directors before, so Eisenberg has to be careful.

Here are a few:

Martin Scorsese: New York, New York (1977)

This movie was a notorious bomb for Scorsese, as it was his follow-up to Taxi Driver. It was highly anticipated at the time, with it pairing Robert De Niro and Liza Minnelli, but the film, which went hugely over budget, was a bust. Scorsese became depressed after its failure but eventually bounced back with one of his greatest films, Raging Bull.

Francis Ford Coppola: One from the Heart (1983)

This movie’s failure led to the collapse of Coppola’s dream studio, Zoetrope, with him spending a staggering $26 million on this musical set in Vegas, with songs by Tom Waits. Why was it such a flop? Partly because Coppola opted to recreate Las Vegas on the Zoetrope soundstages. The movie didn’t even gross a million dollars and sent him into bankruptcy. His next quasi-musical, The Cotton Club, was also a flop. However, both films have since been re-evaluated, with The Cotton Club in particular impressing critics once Coppola released a new cut.

Todd Phillips: Joker: Folie a Deux (2024)

When Todd Phillips announced his Joker sequel was going to be a jukebox musical, it seemed like there was about a 99% chance the movie would be a disaster, but then there was also that small sliver of hope it might be a classic. Suffice it to say, it was a disaster—with it among the biggest flops of all time.

Do you think Eisenberg will pull off what Scorsese, Coppola, and Phillips failed to? To be sure, I’m sure his scale is a lot more modest. I know Eisenberg a bit from interviewing him a few times; he doesn’t take himself super seriously, so the movie probably has a better-than-average chance of succeeding. One thing that’s on his side is that Giamatti is actually a pretty good singer, with him having nailed his songs in the underrated rom-com Duets from the early 2000s.