Hollywood inevitably came calling in the form of producers Don Simpson and Jerry Bruckheimer. Bay had already impressed the duo with his work on the music video for their race car movie "Days of Thunder" (1990). So, at the age of 30, Bay crossed over to features at the helm of "Bad Boys" (1995), about two cops that featured Martin Lawrence and Will Smith. Bay demonstrated an ability to stage impressive action sequences (albeit at the expense of the story) but audiences were impressed enough to the tune of $70 million-plus in grosses in the USA alone and over $160 million worldwide.

Like many filmmakers who came from commercials and music videos, Bay relied on razzmatazz editing and a frenetic pace to the story. He tapped into the same sort of vein for his follow-up "The Rock" (1996). Although the cast was a bit more high brow (featuring two Oscar-winners, Nicolas Cage and Sean Connery), the dazzling effects still held center stage. "The Rock" became a summer blockbuster and typecast Bay as one of Hollywood's premiere action helmers. "Armageddon" (1998), about a meteor on a collision course with the earth, did nothing to dispel that image. The testosterone-driven script revolved around a select group chosen to fly to outer space to save the world, and while Liv Tyler appeared as the nominal love interest, she was underutilized.

For his next project, Bay undertook one that he hoped would confound expectations. "Pearl Harbor" (2001) was a big-budget war epic built around a love triangle. With Bruckheimer once again producing, the director set about recreating that fateful day in December 1941. Clashes with Disney over the film's budget, however, led Bay to walk away from the project four different times during pre-production. It took Bruckheimer's persuasion to convince the helmer to see the project through. Working with a relatively tight budget (estimated at $140 million) and forfeiting his usual fee of $6 million, Bay undertook the biggest risk of his career. Advance word praised the spectacular effects and the battle scenes, but criticized the love story as maudlin and trite. Although the studio heavily hyped the film, there were negative comments by some involved. Writer Randall Wallace was vocal about the changes to his original screenplay and how he and the director did not see eye to eye on things. (Wallace eventually walked away from the project and was replaced by two uncredited scribes.) The actresses, including star Kate Beckinsale along with Sara Rue and Catherine Kellner, were quoted as saying the director was hardly sympathetic to their ideas.

Whatever the case, the film was dominated the early summer box office but "Pearl Harbor" didn't necessarily do for Bay's career what "Titanic" had done for James Cameron's. Rather than follow "Pearl Harbor" up with another strenuous, sweeping mega-action film--like the long awaited new "Superman" movie he flirted with but did not ultimately make--Bay instead opted for a more commerically safe road, reteaming with Jerry Bruckheimer and stars Martin Lawrence and Will Smith to helm the loud, explosive-packed sequel "Bad Boys II" (2003). His next effort, the science fiction actioner "The Island" (2005) showed a (relatively) more restrained hand: this time Bay chose a more story-driven futuristic vehicle, focusing on two characters who live in hope of being relocated from their regimented compound to "the island," the last untainted bio-zone on earth, only to discover that they are in actuality clones who have been created to provide as replacement parts for their donors, who live in the real world. By melding sci-fi parable to his usual trademark slate of bombastic actions scenes, the film was better reviewed (though still prompting split decisions) than most of Bay's previous fare, with no less than the New York Times calling the film "glossy, witty eye candy with some moderately chewy stuff in the middle. This lavish, exhaustingly kinetic film is smarter than you might expect."