The Cruise (1998) on Netflix

Affectionate portrait of Tim "Speed" Levitch, a tour guide for Manhattan's Gray Line double-decker buses. He talks fast, is in love with the city, and dispenses historical facts, architectural analysis, and philosophical musings in equal measures. He's reflective and funny about cruising: he loves it, got in it to meet women, and he'd quit work if he could. His personal life is disclosed in small doses: he takes home $200 a week for 20 hours work, home is his suitcase and wherever he can flop, he's been arrested for going out on the roof tops of skyscrapers to see his city; he stands between the towers of the World Trade Center, spins until he's dizzy, then looks up.