Year: 2006
Ferrari F430 Spider, Pagani Zonda, Speedboat

It seems like the masses have since come around regarding Jay's polarizing lead single from his universally loathed "comeback" album, but back in 2006, people let their hate for the song sweep this otherwise awesome video under the rug. Much was made of Jay's carefree demeanor in the "Otis" video, but look at how much fun he's having here, riding shotgun while Dale and Danica race with reckless abandon through the beautiful streets of Monaco, then splashing hotties in an impromptu speedboat race. High-speed car chases? Dimes in speed boats? Monaco?? A secret lair only accessible by boat? When did Jay-Z became James Bond?