Prolific musicians have been making a killing over the last few years selling the publishing rights to their music catalogs. But the wealthiest acts are making their riches outside of the recording studio. Here are the richest artists who cashed in on their business prowess to become billionaires in this week’s Five For Friday:

#5: Dr. Dre and Kanye West

Dr. Dre and Ye (formally Kanye West) are two rappers who had their billionaire club cards revoked. Ye was worth as much as $2 billion due to his massive deal with Adidas for his Yeezy-branded sneakers. A meltdown that included antisemitic posts on social media caused Adidas to pull the plug on the partnership. Now, Ye’s only worth $400 million, according to estimates.

Dr. Dre, on the other hand, was very close to being the first billionaire in rap. The story goes, as he and record executive Jimmy Iovine were finalizing their agreement to sell Beats by Dre to Apple, Dre got a little overzealous. In a video posted on Facebook with Tyrese Gibson, he boasted that Forbes needed to get ready to change the billionaires list because of the sale. But the deal wasn’t yet public and apparently Apple CEO Tim Cook took the opportunity to shave $200 million off the price, just enough to sink Dre below the billionaire mark. After a divorce, philanthropic spending and luxuries for himself, his net worth is now around $400 million as well.

#4: Diddy

Sean “Diddy” Combs entered the three commas club in late 2022, according to a former Forbes editor who tracks these types of things. Puff Daddy has as many business ventures as he has names. He tackled fashion with Sean John, media with hip-hop-centric Revolt TV and fine liquor with partnerships with Ciroc Vodka and DeLeón Tequila. He still owns the rights to the Bad Boy Records catalog and reports indicate he doesn’t currently have any plans to sell it off.

#3: Jimmy Buffett

Forbes just identified Jimmy Buffett as a billionaire, although the beach bum refuses to confirm or deny his riches. Buffett’s career first took off around five decades ago and has a rabid following for someone so chill. He’s slapped Margaritaville branding on hotels, restaurants and cruises. He even has Margaritaville-themed “55 and better” communities in South Carolina and Florida. Talk about an artist who knows his brand and how to capitalize.

#2: Rihanna

Rihanna was the 2023 Super Bowl halftime show and got paid essentially nothing for it. But she didn’t really need it with a net worth of $1.4 billion, according to Forbes. Rihanna made nearly $100 million per tour more than a decade ago. But it’s her business ventures that have padded her bank account. Her Fenty Beauty line and 30% stake in the Savage X Fenty lingerie line highlight her portfolio. When the latter was looking to possibly go public, it was seeking a $3 billion valuation.

#1: Jay-Z

Jay-Z is worth roughly $2.5 billion, according to Forbes, making him the wealthiest artist. He turned a $56 million investment in streaming service Tidal into $350 million in just 6 years. He also bought the Armand de Brignac champagne brand after he boycotted Cristal. He later sold half of his stake in the brand to LVMH for more than $300 million. Then in 2023 he closed a multi-billion dollar deal with Bacardi for part of his stake in D’usse Cognac. On a much smaller scale, his venture capital firm invested in Stellar Pizza, a Los Angeles-based startup developing pizza-making robot trucks. He’s got so much money, there was talk of him making an offer to buy the Washington Commanders with Amazon founder Jeff Bezos. And he still has big-time music deals.