Just another tragic figure (though if we're being honest, more of a total loser): Shelley Leven (Jack Lemon) in Glengary glen Ross. The poor guy tries so incredibly hard just to keep his head above water—and fails miserably while doing it—that it actually becomes uncomfortable to watch at times. It’s almost as cringeworthy as watching Rupert Pupkin chasing his big break in The King of Comedy.
We've had some truly fantastic suggestions so far! I can't help but think of that guy Harold (I can't recall the actor's name offhand) from The Getaway—you know, the version starring Baldwin and Basinger. In that one, he and his wife (played by Jennifer Tilly) get kidnapped by this intense criminal (Michael Madsen), and well, I think we can all guess how things unfolded from there. I watched the movie with some friends, and honestly, it didn't exactly blow anyone away, but those scenes featuring Harold were absolutely captivating—even though he’s just a supporting character. Afterward, I headed out into town—I remember it was a Saturday—to catch up with a few buddies. It was funny, though; almost everyone asked if I'd seen the "film about Harold"...
Such an incredible movie, and honestly, the soundtrack is just perfection. When you look at Milton's track record, he actually started filming several projects in Hollywood, but he ended up walking away from them after clashing with producers. One of those specific projects was that horror-western, Ravenous—starring Guy Pierce and Robert Carlyle—which ended up being finished and credited to Antonia Bird instead. And then there’s the lead actress, Katrin Cartlidge—who was absolutely brilliant in major films like No Man's Land, Breaking The Waves, Father Hell, and several other Mike Leigh projects (he's really the one who put her on the map)—but sadly, she isn't with us anymore either. She passed away back in 2002 when she was only 42.
A "The Bridge of San Luis Rey"? It stars Harvey Keitel, Gabriel Byrne, Robert De Niro, Kathy Bates, Geraldine Chaplin, F. Murray Abraham, and Samuel Le Bihan—honestly, a film that is just deathly boring.