Back in the early 80s when David Bowie agreed to a new record deal with EMI, it was valued at around $18 million US, making it one of the biggest (if not THE biggest) record contracts signed to that point.
Compared to deals we’ve seen since, though, that’s nothing. In 2005, Bruce Springsteen agreed to stay with Columbia Records for $181 million. Nice, but still not the richest. What about U2? They came to a long-term agreement with their record label in 1993 for $248 million. Again, very good but still not the highest paid.
The all-time record belongs to Michael Jackson who signed a very special and complicated deal with Sony in 2010. But once you sorted about all the complexities, the value of the contract was $312 million Canadian dollars.
Nice work if you can get it.