Everything I know about Deadpool comes from following comic blogs on Tumblr and the frickin awesome new movie, but I'd really like to go and read the comics.

Where's the best place to start? Or is there a certain run that is the best?

I recommend the Hawkeye vs. Deadpool volume. It's short, it's cute, it's a good look at Deadpool's character. The thing about Deadpool is that he has a shitload of comics, but a lot of them are self contained volumes or short runs so they aren't too hard to follow even out of order, especially if you have a vague idea of what is going on in the Marvel Universe around him.
But yeah, Hawkeye vs. Deadpool is great. Read it. Love it. Then read the Matt Fraction run of Hawkeye, because it's equally funny.

Awesome, I'll check those out ASAP! I've read Hawkeye and loved it so I'll definitely start with Hawkeye vs. Deadpool. :)

Yaaay! Someone else who appreciates Hawkguy! Love dat series.