"Church" by T-Pain
This is the dubbed version, used for one of those dance movies, but if you don't mind a ridiculous amount of swearing, the un-cut version is pretty hilarious.
I've said before that I have a soft spot for outlandish hip-hop music, but never about how I got into it in the first place. Here's how: my senior year as an undergrad, I studied abroad in the UK. It was fantastic. However, when I got back, most of my friends had moved on, and I found myself having to start from scratch socially in my last months at the school. Luckily my randomly assigned roommate (since I was gone part of the year I didn't get to choose my own) turned out to be really cool.
She was all about having fun, and I needed all the fun I could get. All but one of my old friends had ditched me, I had capstone classes and grad school application, not to mention my honor's thesis, and my grades from the UK were very late in coming so I wasn't sure I would even graduate. Essentially, I was a mess. But this new roommate of mine new just how to pull me out of it. Thanks to her, I did a lot more laughing than I ever could have otherwise. One of the things she would do is play hip-hop and rap music, preferably with the silliest lyrics possible, and I would laugh and forget my problems for a little while.
That's how I first heard this song.