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Ddey65
http://www.imcdb.org/movie_1004509377-Weird-Al-Yankovic--Dare-to-Be-Stupid.html
http://www.imcdb.org/movie_1004509378-Weird-Al-Yankovic--It-s-All-About-the-Pentiums.html
Vehicle roles?
http://www.imcdb.org/movie_1004509378-Weird-Al-Yankovic--It-s-All-About-the-Pentiums.html
Vehicle roles?
Dare to Be Stupid: running over Al in a stop-motion animated sequence during an instrumental break. I don't know if that qualifies as two or three.
All About the Pentiums: Driven by Al himself with four hot chicks following him as if he's Puff Daddy...
..well, you saw both of them. You'd have to say that the Metro in "Pentiums" ranks four.