5. Illegally Yours (1988)
Director: Peter Bogdanovich
Film purists would probably prefer to not be reminded about Illegally Yours, assuming that they’ve even heard of it in the first place. That’s because Peter Bogdonavich, its ill-fated director, is widely recognized as one of the top auteurs to emerge from Hollywood’s golden era of the 1970s. Coming up under mentor Roger Corman, Bogdonavich transitioned from 1968’s visceral and underrated Targets into 1971’s teen angst masterwork The Last Picture Show. By 1974, he’d blessed cinephiles with three more stellar flicks: What’s Up, Doc?, Paper Moon, and Daisy Miller.
Save for 1985, though, when the critically adored Mask hit theaters, no subsequent year treated Bogdonavich all that well, and 1988 was the worst of all. Squandering all of the goodwill earned from Mask, Bogdonavich foolishly attached himself to the idiotic screwball comedy Illegally Yours. It’s the kind of painfully unfunny and inept flick you’d expect from one of these guys, but not someone who once rivaled the likes of Martin Scorsese and Robert Altman.