Kanye is addressing his girlfriend's father who passed away, respectfully saying that he must have given condolences when Kanye got in a serious car accident. His car was smashed (balled up) - he sings about this in his song Through The Wire.
Bugsy Siegel was an American mobster from the 40s that went to Nevada and built a casino (The Flamingo). The casino was considered legal even though where the money to start it came from was questionable and was built with black market material
There is a dance called "walking it out." In the song, DJ Unk says, "take 2 steps to the left & 2 steps to the right. Bring it back, now I made yall walk it out" He means that by following his instructions, you have done the dance; "walked it out."
I went to art school refers to painting a picture with the back of someone's head after shooting them. Painting a "pollack" (an abstract piece of art on a wall or other surface, after the artist named such) with your brain.