Willie Nelson – $25 million
Greatest Hits: On the Road Again, Family Bible
The Texas-born musician and songwriter Willie Nelson commenced his musical career in earnest with the release of Shotgun Willie Nelson. He is an incredibly colorful character that is famous for his love of cannabis and being an advocate for the drug’s legal usage. Nelson was also a prominent actor and has never faltered in his efforts to reverse the effects of drug prohibition. Nelson infamously ran into a lot of legal trouble for trying to cheat the IRS.
Elton John – $500 million
Greatest Hits: Crocodile Rock, Rocket Man
Elton John is one of the United Kingdom’s most celebrated artists and is world-famous for his emotive and energetic songs. John has enjoyed hundreds of millions of record sales in his lengthy career. He dedicated an entire album to the late Princess Diana following her tragic death, called Candle in the Wind. The lead song continues to be his most successful track. He is one of the well-regarded and popular artists in the world, just behind other titans like Madonna and The Beatles.