Billy Dee Williams | 1984 Jeep Grand Wagoneer | $40,900

Given credit for his role as Lando Calrissian in the Star Wars franchise, Billy Dee Williams is someone who has appeared in The Empire Strikes back, only to reprise the role 40 years after in The Rise of Skywalker. Williams has kept himself busy with painting, which was actually his first love. He was able to fund his art supplies back then with acting, and so he made a career out of it, too.

Williams does not only hold the record for the longest role reprisal intervals, but he is also a long-time owner of a 1984 Jeep Grand Wagoneer. He bought this right after filming Return of the Jedi, and so it really has some sentimental value. It is also his daily ride, so he had it updated with GPS, as Lando needed newer technology after all. He also owns a rather expensive 2017 MB-AMG C43.