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Requiem for a dream isn't a bad movie, but if you happen to have any experience in the drug/crime world, it seems a bit exploitative and silly. Very stylized and nifty but not a favorite. It always strikes me as something that teenagers will - and do - love, and emulate without really getting the point of. Or maybe I didn't, who knows? But I read the book while I was in prison for selling drugs and it felt the same way. By far, it would be the most accessible, least challenging of the three.
Donnie Darko is incredibly creative. It's what I would recommend if I had to pick out of the three for somebody. It's not as accessible as Requiem, but not nearly as challenging as Magnolia. I liked it when it first came out but all of the people I knew who LOVED it kinda irritated the **** out of me and it was hard for me to distance the movie from it's fans. However, years later, I was stuck way out in the country with no ride and only a few movies to kill time with and the directors cut of Donnie Darko was one of them. (I recommend the directors cut, the music is different and there is a bit more to it. Also, the commentary has Kevin Smith with the director). There is a great sense of distance, a feeling like everyone is lost in the world, but there seems to be a governing force guiding things in the right direction. It seems very dark but in the end it really isn't. Also, there's Katherine Ross, who played Elizabeth in Butch Cassidy and the Sundance Kid. She's Donnies therapist and while it's a small role, one of the most powerful scenes hinges on her dialogue.
Magnolia I just watched again for the first time since right after it came out at my girlfriends house on VHS. It was one of those movies that took two tapes. I didn't pick up on a lot of the great things in it when I was younger but watching it now, I really enjoyed it once i got used to the intensity. Watching 9 different characters go entirely to pieces for a little over 3 hours is a bit trying but enjoyable if you're in the right mood. It's done well. Heavily stylized, but not the way that Requiem For A Dream is. There's very little about Magnolia that attempts to be cool, just creative. He really goes out on a limb with some things but I can't fault any of it as unnecessary or pointless. Part of the appeal is how well played things feel.