"Hollywood" premiered on June 23, 2003, on VH1.

The music video for "Hollywood" was filmed at Universal Studios in Universal City, California and directed by Jean-Baptiste Mondino, who previously worked with Madonna on her videos for "Open Your Heart" (1986), "Justify My Love" (1990), "Human Nature" (1995), "Love Don't Live Here Anymore" (1996), and "Don't Tell Me" (2000).

 In the United States, "Hollywood" premiered on June 23, 2003, on VH1. Madonna had long been a fan of the work of French fashion photographer Guy Bourdin since about a decade ago, commenting on his photographs as "They're so sick and interesting. These girls, you have to see the look on their faces — they're really bizarre." Arianne Phillips created the costumes for the video and she described Madonna's looks as an homage to old Hollywood glamour, while trying to be literal as well as conceptual. She paid tributes to stars like Ginger Rogers, Jean Harlow and Mae West. According to Mondino's own words, the concept of the video was: 

"Some kind of artifice that Hollywood can provide, that is so wide and has a graphic story-line about it as well as some humor about it, and to show the beauty, the scariness, the sexiness and the loneliness that one's success can be, 'cause everybody's dreaming about Hollywood, no matter what. The expectation can be very dangerous, and maybe for somebody like Madonna, who might be at a point, to realize that to be on the top is maybe not that important. That's what I feel about the video."

The music video features Madonna in different styles and fashions. It also includes her dripping in twenty million dollars worth of vintage jewels and gowns in several transformations, including an original 25 carat ring and bracelet that was worn by West in the 1933 film, She Done Him Wrong. A real doctor (Dr. David Kish) was hired by Madonna to administer the fake shots, since she wanted to make the scenes appear real. The first day of shooting took place on June 2, 2003, and the scenes shot included the wall-of-mirrors, the massage, the botox injection and the ballet dancing sequences. The next day started with the French maid, the motel TV, the telephone conversation and the glamour shot scenes. Henry Keazor, one of the authors of Rewind, Play, Fast Forward: The Past, Present and Future of the Music Video, noted that Madonna exposed herself during the interventions portrayed in the video, by playing with the rumors and the stereotypes surrounding her.