1. “Feelin It” Video (1996)
Jay-Z’s Jamaican moment: “Feelin It” was shot in Negril, Jamaica
One of the lesser known singles on Jay’s debut Reasonable Doubt (but one of our favorite songs by him, ever) the champagne-smooth “Feelin It” is also the subject of one of his least remembered music videos. But it’s a classic nonetheless, especially for those who appreciate the finer things in life— like gold jewelry, yachts, and lovely Jamaican scenery, female and otherwise. As with some of Jay’s other videos from that period, he’s depicted as a Tony Montana figure in Scarface-inspired mob scenes, showing off next-level expensive jewelry (note the yellow gold Presidential Rolex, likely a rap video first). Except instead of gaudy ’80s Miami, the setting for Jay-as-Tony’s cigar-scented hostile takeover is a classy, old-world villa in Negril.