Lady Gaga is the list's highest-ranking newcomer, at No. 4, with $62 million in earnings.
Winfrey reclaimed the title from last year's No. 1, Angelina Jolie, who dropped all the way to No. 18.
The Queen of Talk earned a staggering $315 million over the last year. It's the fourth time she's been in the No. 1 slot.
Collectively, the 100 actors, actresses and musicians on the list made $4.7 billion during the past year, up from $4.1 billion in the year-ago span.
Beyonce Knowles climbed two spots, to No. 2, after a successful year touring and continuing to grow her empire, which includes music, fashion, fragrance, and a slew of endorsement deals, for $87 million in earnings.
Director James Cameron rode the box office success of "Avatar" all the way to No. 3, returning to the list for the first time since 1999, with $210 coming in over the past year.
Tiger Woods stayed at No. 5, despite his sex scandal, which cost him some endorsements. He took in some $105 million during the past year.
Aside from Lady Gaga, other newcomers of note include "Twilight" co-stars Robert Pattinson (No. 50) and Kristen Stewart (No. 66), Conan O'Brien (No 51), the Black Eyed Peas (No. 16), Robert Downey, Jr. (No. 73) and Chelsea Handler (No. 98).
Rounding out the Top Ten: Britney Spears at No. 6 ($130 million in earnings, mostly from a successful world tour;); U2 at No. 7 ($130 million), Sandra Bullock at No. 8 (her successful films and high-profile split with husband Jesse James kept her name in the news; Johnny Depp at No. 9 (the top earning actor on the list, with $75 million, and Madonna at No. 10 ($58 million).