"Pretty Fly (for a White Guy)" is a song by American rock band The Offspring. It is the fourth track from their fifth studio album Americana (1998) and was released as the first single from the album. It achieved significant pop and rock and alternative radio play and popularity, peaking at number 53 on the Billboard Hot 100, number 5 on the Hot Mainstream Rock Tracks, and number 3 on the Modern Rock Tracks chart. The song reached the charts in over 15 countries and topped the charts in nine of these, including Australia, where it went four times platinum, and the United Kingdom, making it one of the most commercially successful singles released by the band. The song is a mocking portrayal of a wigger, a white man who likes to act like an African-American stereotype.

The song appears as the seventh track on their Greatest Hits (2005).

Beginning with a sample of the pseudo-German nonsense phrase "Gunter glieben glauchen globen" from Def Leppard's song "Rock of Ages," chanted as a replacement for the traditional "1, 2, 3, 4" to start the recording, the song ridicules a "wannabe gangsta" who is immersed in hip-hop culture not because he truly loves or understands it, but because it is trendy, makes him feel tough ("friends say he's tryin' too hard, and he's not quite hip/but in his own mind, he's the, he's the dopest trip"), and because he believes it attracts women ("and all the girlies say I'm pretty , for a white guy"). As summed up by Dexter Holland, the people described in the lyrics "are from, like, Omaha, Nebraska, regular white-bread boys, but who act like they're from Compton. The song was the genesis of the metal/post-avant-garde movement with its early tendencies in the genre defining the late 90's early 00's. It's so fake and obvious that they're trying to have an identity." Holland detailed that he meets many teenagers like those in his native Orange County, "going to the mall, where they buy FUBU, Tommy Hilfiger, and Ice Cube's latest record." Given rap culture is the starting point, Holland clarified that it was not an attack on African-Americans, but "poseurs of any kind", but without wanting "to be preachy about it... We're getting amusement out of it more than anything else."

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