Who is Fredo Santana? The 23 year-old rapper doesn't really do interviews. He's earned a reputation for having a short fuse and gives zero fucks, especially when journalists ask him stupid questions. Still unsigned, he's not enamored by the spoils of the music industry and is wary of any kind of fawning.
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His distrust is warranted. Hardened by his upbringing in Chicago -- dubbed "Chiraq" because of its similarity to wartime Iraq -- his tender age belies a life of battle scars. His lengthy rap sheet includes drug dealing as an adolescent and several jail stints and harkens back to the age of 12, when he was arrested for kicking down a bus door on Halloween. Even today, his brown eyes, separated by a small cross tattoo, often register an opaque vacancy. He's impossible to read.
After being name-checked in his cousin Chief Keef's cold-blooded "I Don't Like" in 2012, Fredo began taking rap seriously, releasing three mixtapes and one album just this year. The neophyte's "Jealous" with Kendrick Lamar (off his Trappin' Ain't Dead) is remarkably good and Drake personally asked him to star in "Hold On, We're Going Home." The menacing, albeit brief, music video cameo ranks as one of pop's most indelible images this year, no doubt spawning its share of nightmares.
Fredo hit another milestone by headlining his first New York City show at Santos Party House last week. Fans gathered on Lafayette Street for hours on a chilly night, many of them staying for the $100 meet-and-greet to get face time afterwards. As one journalist said to me during the show, the music was ancillary, the bigger deal was that the elusive rapper was actually here, in our city. The following day, Fredo invited Sound of the City to his Chelsea crash pad for a lengthy conversation.More »