The “vanity project” is an institution as old as Hollywood itself, but only with the advent of free agency and the modern-blockbuster sensibility did the passion projects of A-list actors truly cause collateral damage at the box office. The ur-film here is the most infamous comic flop of all time, Ishtar. Off a $55 million budget it pulled in a paltry $14.3 million dollars—very costly, especially in 1987 dollars. But what makes Ishtar so notorious is the pedigree of those involved: the great comedy doyenne Elaine May wrote and directed the film with Warren Beatty and Dustin Hoffman, at the heights of their powers, as the leads (and cinematography by the great Vittorio Storaro to boot). All that legendary talent squandered on such a failure just smarts on a philosophical level.

But leave it to Kevin Costner to put them to shame: even though Waterworld earned all the bad press, his follow-up The Postman truly broke the bank with only $17 million off an $80 million budget. It was a bomb so bad, it almost sank Costner’s then red-hot career as an actor-director. He wouldn’t direct another film until 2003. Yet, that’s a drop in the bucket compared to The Adventures of Pluto Nash. Eddie Murphy’s bizarre space comedy proved one of the costliest flops of all time earning a mere $7 million against a $100 million budget, a failure so bad it caused Warner Bros. president of production Lorenzo Di Bonaventura to publicly disown it.

However, in terms of pure notoriety, Gigli takes the cake, even if it was (marginally) less costly ($7 million gross against a $54 million budget) and (barely) better reviewed (6% on the Tomatometer versus 5%) than Pluto Nash. The afterglow of both Ben Affleck and Jennifer Lopez’s megawatt stardom misfiring at the same time will always burn bright on the inner eyelid of critical and popular consciousness.