After more than a decade as one of the hardest-touring bands in the land, the Roots accepted Jimmy Fallon's offer to join him on his new Late Night show in 2009. The gig forced them to start waking up at 5 a.m. every day – but it also allowed them to jam on national TV with stars from Bruce Springsteen to Carly Rae Jepsen, and exposed them to millions of new fans. "Financially, it's a great ending," drummer Ahmir "?uestlove" Thompson told us at the time. "We get to be our own island again."
Potential payday: The exact number the Roots made is unknown, but it's probably somewhat less than the $17 or $18 million Mariah Carey is reportedly getting to judge American Idol.
Downsides: Very few of these jobs exist. You'd have better luck playing Mega Millions.