Reared in poor, rural Mississippi , Oprah today is the richest woman in entertainment and the only black female billionaire. In the late 1980s, following the debut of her super-successful syndicated talk show, Oprah earned $2 million a year. Today, she pockets an estimated $225 million annually from TV (including shows starring Dr. Phil McGraw and Rachael Ray, produced by Oprah's Harpo Productions), satellite radio, magazines and other multimedia endeavors.
She could have easily disappeared into pop obscurity like the other frothy pop tartlets ( Cy ndi Lauper, Neneh Cherry) who came to fame on nascent MTV in the early 1980s. But Madonna's masterful manipulation of her image and the press, combined with an astute business sense, have crowned her as one of entertainment's wealthiest and most enduring acts. While her albums don't sell like they used to, her concerts still set attendance records all over the world, grossing $1 billion over the course of her 20-year career. The Material Girl's portfolio is also crammed with expensive items like contemporary art, real estate and a wardrobe of no small historical significance.
The Canadian chanteuse's exclusive five-year gig at Caesar's Palace in Las Vegas has vaulted her into fifth place on our list of The 20 Richest Women in Entertainment. Dion's stationary extravaganza is more profitable than one that requires paying roadies in every major city in the world. An estimated 140 million albums sold worldwide hasn't hurt her bottom line either; her single 'My Heart Will Go On'--the theme song for the blockbuster Titanic--sold over 15 million copies alone.
The Long Island songbird's career exploded in 1990 with her debut album released under the guidance of Columbia Records' boss Tommy Mottola. (The two endured a tempestuous five-year marriage before divorcing in 1998.) Her career was seriously derailed with the 2001 release of Glitter, a critically slammed semi-autobiographic soundtrack and movie. A year later, Columbia bought out her contract for a reported $28 million. No one could have anticipated her extraordinary comeback in 2005 with the bestselling The Emancipation of Mimi. To date, the pop diva has sold 160 million albums.
As the youngest of the famous Jackson clan, Janet has always enjoyed the spotlight. But it wasn't until 1986, with the release of her breakout, platinum-selling album Control, that she came into her own. Since then, Michael's kid sister has sold over 50 million records worldwide and landed 10 No. 1 singles on Billboard's Hot 100. Her latest album, 20 Y.O., hardly made a blip on the charts, but don't count Miss Jackson out. Tours have proven a substantial cash cow for the seasoned performer, and she hits the road again in March.
The highest-paid female actress in history, this Academy Award winner grew up in Smyrna , Ga. , and, after high school, followed her older brother, actor Eric Roberts, to New York . After her breakout role as a hooker with a heart of gold in Pretty Woman (1990), Roberts went on to become the first actress to break the $20 million salary mark for a movie, which had become standard for Hollywood 's male superstars. Roberts still holds the world record for highest payday ever earned by an actress: She pocketed $25 million for the 2003 flick Mona Lisa Smiles, which amounted to nearly 40% of what the film grossed stateside.
The former backup dancer from the Bronx has gone on to become a multimedia powerhouse in both movies and music. She commands upwards of $15 million per movie, but she's lately taken far less to focus on pet projects. While her albums once sold millions, her last, Rebirth, released in 2005, suffered from disappointing sales. Lopez is a well-rounded businesswoman with several other revenue streams, including a clothing line, an incredibly successful perfume line, a Pasadena, Calif.-based Cuban restaurant called Madre's, and a new reality show on MTV.
The daughter of a soap star (John Aniston of Days of Our Lives ), Aniston eclipsed her father's TV fame with her turn as Rachel Green on the eternally popular sitcom Friends . In the show's final years (it ran 10 seasons), Aniston and her castmates struck what was then a record deal: $1 million each per episode. Her film career has been hit or miss: Bombs like Rumor Has It and Derailed have been offset by box-office bonanzas like Bruce Almighty and The Breakup. The press-averse Aniston is magazine cover gold, which has kept her divorce from Brad Pitt in the headlines for some two years and counting.
At age 20, the fraternal twins preside over the tween retail empire Dualstar Entertainment Group. Established in 1993, it sells $1 billion worth of merchandise worldwide a year--everything from videos to hair-care products--primarily through Wal-Mart Stores and the twins' Web site, MaryKateAndAshley.com. Last year, the twins starred in print advertisements for high-end designer Badgley Mischka. Not bad for former child sitcom stars (Full House) who haven't appeared in a hit movie or television show since.
In just a few short years, Spears went from an obscure teen actress on the Disney Channel's short-lived The New Mickey Mouse Club to one of the most successful pop singers in the world with her 1999 debut album, ...Baby One More Time . During her brief career, she has sold 75 million records and enjoyed seven hit singles. Her tours have grossed $145 million to date. Spears took the last few years off, a period in which she married, had two children, then ultimately filed for divorce from backup dancer Kevin Federline--a series of events that helped earn her tabloid queen status.. Word is Britney is back in the studio recording a comeback album.
Bullock rose to fame with 1994's Speed and soon went on to become one of the highest-paid actors in Hollywood . She banked her biggest paycheck for Miss Congeniality 2: Armed and Fabulous , released in 2005, which grossed just over $100 million worldwide. Fortis Films, her production outfit, produced many of her films, including both Miss Congeniality films and Two Weeks Notice. It also produces ABC's The George Lopez Show, now in syndication.
Diaz is Hollywood 's only actress besides Julia Roberts to break the $20 million-per-film salary mark. The former model got her big break in 1994 as an unknown starring opposite Jim Carrey in The Mask; she went on to star in blockbusters like There's Something About Mary and the Charlie's Angels films. Thanks to commercial disappointments The Sweetest Thing and In Her Shoes , her salary has since been slashed. But she's still one of Hollywood 's most bankable (and prolific) stars.
While she hasn't sold as many albums as fellow former Mickey Mouse Club castmate and pop tart rival Britney Spears, the Grammy Award winner's latest album, Back to Basics, went to No. 1 on the charts in 13 countries. Aguilera has sold over 20 million albums to date, while her tours have grossed some $50 million. Endorsement deals with Verizon and Pepsi, among others, have also bolstered her bottom line.
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