Sleepy Hallow is Tegan Chambers, a Jamaican-American drill rapper from the Flatbush section of Brooklyn. He came to prominence in 2020 with "Deep End Freestyle," which features vocals by Fousheé and peaked at #80 on the Hot 100. That earned him a contract with Winners Circle Entertainment and RCA Records. "2055" is a song from his debut album, <b>Still Sleep?</b>
<i>I just wanna slide Parties in the sky like it's 2055</i> When Prince sang of wanting to "<a href="https://www.songfacts.com/facts/prince/1999">party like it's 1999</a>," he was advocating enjoying ourselves while we can, before we're all wiped out by the bomb. Sleepy Hallow's lyrics are more melancholic as he raps about his struggles with street life, fake friends and lying women. Because his heart is so cold, Sleepy doesn't want to get involved in the gangsta lifestyle and prefers to chill on his own.
New Jersey producer Great John supplied the somber beat. Great John produces most of Sleepy Hallow's songs, as well as those of Sleepy's friend, fellow drill rapper Sheff G.
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