Weezer returned with the darker Pinkerton in 1996, having scrapped their previous plans to record a space-themed rock opera as their sophomore album. Cuomo wrote the album's ten tracks while studying at Harvard, drawing upon such themes as groupies, fan mail, lesbians, and Japanese women. While the album didn't yield any hit singles, fans treasured it as a stronger release than the band's debut. Nevertheless, Weezer once again went on hiatus following Pinkerton's supportive tour, and bassist Sharp permanently left the lineup to devote more time to his other band, the Rentals (Sharp was later replaced by Bostonian Mikey Welsh). With little news coming from the Weezer camp by the dawn of the 21st century, many assumed the band had broken up. Cuomo gave a few surprise solo shows in Boston during 1999, however, and announced the following year that a third Weezer release was forthcoming.

The release did not see the light of day until 2001, as Cuomo was waiting for braces to come off his teeth before recording would commence. Known as The Green Album, the record spawned the hit singles "Hash Pipe" and "Island in the Sun." 2002's Maladroit did not fare as well, but Weezer returned to hitmaking status with 2005's Make Believe, which earned the band a Grammy nomination for the song "Beverly Hills." The album's content was partially inspired by Cuomo's discovery of meditation, which he had practiced intensely during the three previous years. Cuomo had also been recording homemade demos since the band's inception in 1992, and he gathered 18 of them for a 2007 solo compilation, Alone: The Home Recordings of Rivers Cuomo. ~ Greg Prato, All Music Guide