The group's early gigs involved playing straight Gypsy music at Russian weddings, but their music soon evolved into the hyper-kinetic explosions that earned them a solid following among New York's downtown hipsters. The band issued a single in 1999 entitled When the Trickster Comes a-Pokin', quickly followed by their debut full-length, Voi-La Intruder, which was produced by Nick Cave & the Bad Seeds drummer Jim Sclavunos. Solofar and Kazatchkoff were replaced by accordionist Yuri Lemeshev, who hails from the Russian island of Sakhalin, and two Israelis, guitarist Oren Kaplan and saxophonist Ori Kaplan, who despite their similar names aren't related. Hütz helped bolster the band's popularity by becoming somewhat of a celebrity in the downtown scene, in part fueled by his Thursday night DJ gigs at Bulgarian club/restaurant/bar Mehanata, where he played Ukrainian, Gypsy, rai, and flamenco music for a crowd of artists, models, Ukrainians, Russians, Gypsies, and Bulgarians with tendencies toward exuberant dancing and smashing plates.
In the spring of 2002, Gogol Bordello embarked on a European tour and performed as part of the Whitney Biennial, bringing their music to a whole new audience. Voi-La Intruder came out around that same time, followed that fall by another album, Multi Kontra Culti vs. Irony. The East Infection EP came out in March 2005 before Gogol Bordello made their Side One Dummy debut that August with the aptly titled Gypsy Punks. By this point, though the band's cast no longer included Ori Kaplan, it did boast bassist Rea Mochiach and dancers/percussionists Pam Racine and Elizabeth Sun. Aside from leading the band, Hütz also lent his hand to acting when he was cast as Alex in 2005's Everything Is Illuminated (based on the critically acclaimed book) after Gogol Bordello attracted the attention of the film's producer. The bandmembers soon got to work on their next album, however, switching to bass player Tommy Gobena and utilizing the talents of producer Victor Van Vugt to help them craft their fourth full-length, Super Taranta! Wildly praised by critics, who pasted the album all over their year-end lists, Super Taranta! (as well as the band's increasingly physical live shows) made them indie rock heroes. Live from Axis Mundi was released in 2009, followed by the group's Rick Rubin-produced fifth studio offering, Transcontinental Hustle in 2010.