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40. "Izzo (H.O.V.A.)" (2001)

One of Jay's biggest early commercial hits – it peaked at Number Eight on the Billboard Hot 100 – this Kanye West-produced track features an exquisitely used sample from the Jackson 5's soaring "I Want You Back." "I grew up in the Marcy Projects in Brooklyn, and my mom and pop had an extensive record collection," Jay told NPR's Terry Gross in 2010. "So Michael Jackson and Stevie Wonder and all those sounds and souls – Motown etc., etc. – filled the house. So I was very familiar with the song when Kanye brought me the sample. It was just such an interesting and fresh take on it that I immediately was drawn to it."