I've never hailed a taxi.
I feel that this is a failing on my part, and one that must be corrected before I can even pretend I'm a New Yorker.
In fact, I think I've only been in a "real" taxi once or twice-- coming home from the airport late at night. No hailing required-- just get in the line for cabs and pop into the next one that pulls up.
Except for the airports, Brooklyn and Queens don't generally rely on yellow cabs. We have car services. Same pay-by-mile/time system, but they aren't hailed. You just give 'em a call and they pick you up. Car services are prevalent; there's one less than a block away from our apartment that we used to catch a 6 a.m. flight to Ohio.
Paul has hailed a cab or two for work, but I've never seen him do it. Except for going to or from the airport, we had rarely even been in a New York cab or car service vehicle together until Saturday night. We were with some friends in Queens, it was 4 a.m., and a subway ride would have been 90 minutes on a good night. Probably closer to two hours. Or more.
So we splurged on a car service, the first time we've ever done so after a night out. Warm! Comfortable! Quick! I just tried not to pay attention as Paul handed over two $20 bills for the convenience.