1. Jennifer Aniston vs. Angelina Jolie
Aniston: $27 million
Jolie: $14 million
Jolie may have gotten the guy (Hollywood hunk Brad Pitt, that is), but Aniston has the fatter wallet. The former Friends star banked $27 million between June 2007 and June 2008, thanks to a slew of upcoming films, including Marley & Me and He's Just Not That Into You. She also earns big money on Friends syndication and a Smartwater endorsement deal.
2. Miley Cyrus vs. Jonas Brothers
Cyrus: $25 million
Jonas Bros.: $12 million
The Jonas Brothers may be the next big thing, but the Hannah Montana dynamo still has them beat at the bank. In addition to Cyrus' 70-date Best of Both Worlds concert tour, which raked in some $50 million, the 15-year-old sensation has a book deal, a TV series and several movies in the works.
3. Ben Stiller vs. Will Ferrell vs. Adam Sandler
Stiller: $40 million
Ferrell: $31 million
Sandler: $30 million
Tinseltown's funnymen may be equally funny, but they're not equally rich. Stiller proves the best paid this year, pulling $40 million over the 12-month period--an impressive sum given his year at the box office. His flick The Heartbreak Kid was one of the worst-performing movies of his career, garnering a paltry $37 million in domestic theaters. Of course, the big budget flop didn't prevent lofty salaries for this summer's Tropic Thunder and the upcoming Night at the Museum 2.
4. Ashley Tisdale vs. Vanessa Anne Hudgens
Tisdale: $5.5 million
Hudgens: $3.2 million
While screech-worthy stars each, the ladies of High School Musical have added new and different entries to their resume. Tisdale's include a Disney Channel series, a straight-to-DVD movie and some endorsement work. Hudgen's: an album, a flick and some endorsements as well. In the last year, the former has proved more lucrative than the latter.
5. Jerry Bruckheimer vs. Steven Spielberg vs. George Lucas
Bruckheimer: $145 million
Spielberg: $130 million
Lucas: $50 million
Move over Spielberg, Bruckheimer takes top honor as Hollywood's top-earning producer. He raked in $145 million, thanks in large part to Pirates of the Caribbean: At World's End, the top-grossing movie of 2007. The much-hyped flick plundered $961 million at the worldwide box office. Similarly successful, not to mention highly lucrative: National Treasure: Book of Secrets, which banked $457 million in theaters. His small-screen fare--the CSI franchise as well as Cold Case and Without a Trace--adds an estimated $70 million to his coffers.
6. Howie Mandel vs. Drew Carey vs. Jeff Foxworthy
Mandel: $14 million
Foxworthy: $13 million
Carey: $12 million
Deal or No Deal has proved a great deal for its host Mandel, who out-earns his fellow hosts by only a small margin. Thanks to the addictive show, the germophobic and now best-paid game show host banked $14 million over the course of the year. Also fattening his wallet: endorsement deals and stand-up gigs.
7. Tyra Banks vs. Heidi Klum
Banks: $23 million
Klum: $14 million
When it comes to supermodels turned super-personalities, Banks and Klum seem to have a lock on the market. But while both continue to score shows and deals, Banks is the bigger earner. Among her projects: two hit shows--America's Next Top Model and The Tyra Banks Show--and larger production deal.
8. David Letterman vs. Jay Leno
Letterman: $45 million
Leno: $32 million
NBC's Leno may earn higher ratings than CBS' Letterman, but he comes up short in cash. Turns out it pays to be your own boss: Unlike the NBC host, Letterman owns a stake in his late-night show. That played to his advantage last December, when his production company hammered out a deal with its striking Writers Guild members to get them back to work ahead of others.
9. Sean (Diddy) Combs vs. Shawn (Jay-Z) Carter
Carter: $82 million
Combs: $35 million
While hardly the rivalry rap has long been famous for, Jay-Z has Diddy beat in this money match-up. And with good reason, given the year the Brooklyn, N.Y.-born hip hop demigod has had. Between June 2007 and June 2008, he released a platinum album, signed a 10-year, $150 million deal with concert promoter Live Nation and tied the knot with longtime girlfriend Beyoncé Knowles.
10. Ryan Seacrest vs. Simon Cowell
Cowell: $72 million
Seacrest: $31 million
American Idol's leading men have had little trouble banking big money. But while Seacrest is constantly cutting deals, Cowell remains the earnings champ. The cranky judge on America's most-watched TV show pulled down $45 million from Idol, $15 million from Britain's Got Talent and The X Factor (he owns both and appears as a judge on each) and $12 million of profit from his record label.