The Knocked Up star headed to Hollywood to practice his craft after college and upon receiving his first big pay cheque, he splashed out on a brand-new Nissan so he could drive himself around.
But Rudd admits things went downhill from there, and he ultimately had to relocate to Manhattan, where he could rely on public transportation, because he was too much of a liability behind the wheel.
He tells U.S. TV host David Letterman, "I always wanted to live in New York... I thought if I'm going to go there, to New York, I'll know the time if it's right, and that's exactly what happened.
"It started with a crazy series of events when I bought a car and then two weeks later it was stolen... And then I rented a car; the next day, crashed by a hit-(and)-run driver. So a friend of mine lent me his car, I drove down a hill, it hydroplaned on some water and I smashed that car into another car. We are zero-to-three with cars in a span of about three days.
"Then I rented another car, again in a car accident... So I came here (to New York) and I got an audition for the Manhattan Theatre Club... I went back (to L.A.), rented a car, put my stuff in a storage unit. The next day, one in the morning, I'm lying in bed, I hear a crash. I look out the window and the car I had rented, totalled by a hit-(and)-run driver. Five cars in a total of about six days. I moved here the week later and I've never been back (to live in L.A.)."