The quickest way to do this is using Free Skate. From the main menu, go to Ranked & Free Skate then select each level below and get hit by the corresponding vehicle. Easiest way is to watch their route and just stand and wait for them to loop back around. Once you get hit you can end the session, and then press level select to go to the next one.
The levels below are listed in the order they appear on the level select menu:
THPS1 - Downtown - Minneapolis - Taxi
THPS1 - Streets - San Francisco - Trolley/Tram
THPS2 - School II - Southern Cali - Golf Cart
THPS2 - NY City - New York - Taxi
THPS2 - Philadelphia - Pennsylvania - Bus
Once you get hit by the final vehicle a challenge should pop up in the top right followed by your achievement.