Since he had only been earning a limited salary, Jet Li obtained a two-year exit permit and settled in San Francisco with a Chinese actress who would briefly become his wife. "The Master" (filmed in San Francisco in 1989 but not released until 1992) was a minor modern-day kung fu thriller, more notable as the first time Jet Li worked with director Tsui Hark. Instead of returning to China in 1990, the actor settled in Hong Kong, where he attempted to rejuvenate his sagging career by signing with Golden Harvest. His breakthrough screen role came in 1990 when Tsui Hark cast him as real-life folk hero Wong Fei Hung in "Once Upon a Time in China". Despite critical carping over Jet Li's relative youth and his training in another martial arts discipline, the period piece offered the performer a strong role and he more than met the challenges exhibiting the requisite stoic aura. He went on to reprise the role in two sequels (in 1992), but an ankle injury forced the use of a double in several fight sequences. Nevertheless, Jet Li dominated the films in a role many felt he was born to play. The actor, however, felt financially under-appreciated and after a series of disputes parted company with Golden Harvest. (He was replaced by another actor for two sequels before resuming the franchise in 1997's "Once Upon a Time in China and America", which can be qualified as a kung fu Western.) Over a five year period (1992-97), Jet Li appeared in over two dozen films of varying quality. He scored as another martial artist folk hero "Fong Sai Yuk" (1993) and played his signature role of Wong Fei Hung in the uneven "The Last Hero in China" (also 1993), which he also produced. Additionally, he starred in the biopics "Tai Chi Master" (also 1993) and "New Legend of Shaolin" (1994), By the time of "Black Mask" (1996), an attempt to create a new franchise based on a popular Hong Kong comic book, his career was on the wane once again.

Despite numerous offers from bigwigs like Oliver Stone and Quentin Tarantino, Jet Li took his time following fellow HK actors Jackie Chan, Michelle Yeoh, Maggie Cheung and Chow Yun-Fat to L.A. At one time he was attached to a Jean-Claude Van Damme vehicle and withdrew just before filming. At last, in 1998, after the Asian economy dropped and film production suffered, Jet Li appeared in his first American studio film, playing the seemingly unbeatable martial artist villain opposite Mel Gibson and Danny Glover in the successful sequel "Lethal Weapon 4"—Li provided much of the heavy action lifting in the aging franchise, staying stone-faced while Gibson fired corny jokes at him (That same year the martial artist had another major Hong Kong hit, Wei Tung's "Sat sau ji wong" playing a reluctant rookie hit man opposite a seasoned veteran played by Eric Tsang).

Producer Joel Silver was sufficiently impressed with Jet Li's performance in his "Lethal Weapon" sequel that he signed the actor to headline his second major American film, envisioning the actor to have Jackie Chan-style crossover success—but replacing Chan's comedic bent with a romantic leading man edge. "Romeo Must Die" (2000)—directed by veteran cinematographer Andrzej Bartkowiak (who filmed Li in "Lethal Weapon 4") and choreographed by Li's longtime stunt coordinator Corey Yuen--attempted to meld a Shakespearean tragic romance to the high-kicking kung fu genre, pairing Jet Li with hip-artist Aaliyah as a star-crossed couple caught in the middle of a war between racially divided mobs in San Francisco. The film performed solidly at the box office, though critics, while praising the actor's physical prowess, decried the seemingly unnecessary use of computer-aided effects in the action sequences.

After arriving in Hollywood, Li spent much time expanding his English vocabulary and took a hiatus to marry and see his wife through her pregnancy, turning down Ang Lee's offer to star in "Crouching Tiger, Hidden Dragon" (2000). Inspired by his vow to protect his wife and child, Li received story credit on his next film, "Kiss of the Dragon" (2001), in which he plays a Chinese intelligence officer in Paris who comes to the aid of a single mom (Bridget Fonda) turned into a junkie hooker by a corrupt cop who kidnapped her daughter—the film mixed elements of writer-director Luc Besson's cult hit "The Professional" (1994) with Li's Bruce Lee homage "Jing wu ying xiong" (1994) a.k.a. "Fist of Legend" (Besson wrote the screenplay for "Kiss," a rare U.S.-Asian-French collaboration).

Next was "The One" (2001) for writer-director James Wong, which added a sci-fi element to Li's established genre, a garbled but often visually arresting tale in which Li plays both the hero Gabe Law, a popular and peaceable veteran of the Los Angeles County Sheriff's Department, and the villainous Gabriel Yulaw, his doppelganger from a parallel universe who by murdering his other-dimensional alter ego increases his strength, stamina and power to take over the multiverse.

The actor then segued into one of his greatest cinematic triumphs, "Ying xiong" (2002), which was released in the United States in 2004 under the title "Hero." Li teamed with celebrated writer-director Zhang Yimou—known more for character dramas than kicks and fisticuffs—Australian cinematographer Chris Doyle and Li's fellow Asian martial arts stars Zhang Ziyi, Tony Leung, Maggie Cheung, Daoming Chen and Donnie Yen for the big-budgeted tale set at the violent dawn of the Qin dynasty, circa 220 B.C., where the soon-to-be first Emperor is on the brink of conquering the war-torn land and three of his most passionate opponents (Cheung, Leung and Ziyi) are trying to assassinate him, opposed by the indomitable Li as Nameless, a lowly policeman who faces off against powerful forces. The film become a phenomenal hit in Asia and Europe, and was nominated for an Oscar in 2003 in the foreign language category before its North American release in 2004.