Well gents, consider this a motherfucking gauntlet thrown down.
These are, without a doubt, two of the most punishing movies I have ever seen.
First up, is Don's Plum. This movie was filmed prior to DiCaprio's mega-fame gained from Titanic as favour to a friend of his. And subsequently buried by DiCaprio because of the content of the movie. That content being balls-to-the-wall misogyny.
The plot is similar to an un-eventful version of Diner. Four friends meet at a shitty restaurant every week and must each bring a new girl. The purpose of this is basically to terrorize and shit on these women. It's really fun! No, it's not, it's fucking brutal. Through the entire movie the women are treated like shit, and the four dudes (Tobey Maguire included) are portrayed as being pretty cool guys for doing it. The film itself is fairly stylish, but pretty much every time a character opens their mouth your soul will die a little.
All that being said, I definitely enjoyed watching DiCaprio be a foul-mouthed fucking asshole and will surely, in the future, troll fans of his by recommending this film. Similar to Shatner's racist cop blasting off n-bombs in The Intruder, a very small portion of me enjoyed DiCaprio as misogynistic garbage. Tom Cruise's character in Magnolia has absolutely dick-all (reference intended) on this guy.
0-slash-5 "fucking cunts" out of 5
Now to the other end of the terrible rainbow, let me recommend to you Tiptoes.
First of all, here's the most insanely bad part about this movie up front: Gary Oldman plays a midget. That's right. A full sized person with a full sized (presumably) brain decided "huh, why not play a midget? I am limited only by my talent!" For this reason alone, Tiptoes has already bested (worsted) Riding on the Bus with my Sister for wildly inappropriate and offensive casting. However, where Riding on the Bus with my Sister contained some fucking hilarious dialogue, this movie is just punishingly bad.
Once you get over Oldman-as-little-person (not easy) you will uncover a rich potpourri of movie failures. This movie telegraphs everything; it goes on forever; there are no likeable characters; it is saccharine to the point of blasphemy (as in, because this movie exists, there thus must be no God); and on and on. Watching this movie probably took me a half hour longer than it should have because I had to constantly pause the DVD and press the heels of my hands into my eyes until I could no longer see.
Again, 0-slash-5 midgets, I mean dwarves, I mean little people (seriously movie, pick a fucking term) out of 5
PS If you really want a challenge, watch them back-to-back. Liquor helped me do it; I recommend liquor.