Randy Jackson and Simone (35 Years)
While the general public knows Randy Jackson as one of the panel judges on the smash hit show, American Idol, Jackson actually got his start as a jazz fusion and rock bass player, where he enjoyed incredible success for many years. The combination of his accomplishments as both a musician and American Idol judge has allowed him to snag the very attractive, singer/songwriter, Simone who also happens to be just shy of 4 decades younger than Jackson.