NASCAR 14

This will come naturally over the course of a season. With the AI on easy, you can easily get 40 or so passes per race by starting in 43rd position. Multiple passes of the same car during a race also count.

Puppy's solution certainly will work. But, if you're in a hurry, like me, this can be done in single player. Also, I was going for the 2,400 points in a season and 20 poles on my first play through. I didn't want to be starting from 43rd.

I used Atlanta. Fast and wide, makes passing possible high, low or the middle. AI set to stoopid, 0%. I did two 32 lap races and passed around 150 cars each race. 30 second lap times are possible, even in traffic. That gets it done in less than 45 minutes, even with load times. (conservative estimate) It pops when you pass the 250th car mid-race. You could probably do a 65 lap race and dump out when it pops.