Don't ride with music anymore. In NY in the '70s, I did, but it did not end well.
I prepared for one particularly insane city ride by making two identical cassette mixes and giving my buddy a second Walkman; the idea was that we would be listening to the same tunes at the same time. After fortifying ourselves with various herbal supplements and putting a six-pack of German beer in my backpack, we warmed up riding down Park Avenue, and then launched into the tunnel under (what was then called) The Pan Am building with no lights-- the tunnel itself is barely lit, goes downhill with a steep curve, and has narrow lanes and no shoulders-- while listening to Pat Benatar. (Pretty sure it was "Heartbreaker.") It was GREAT! Shot out of the tunnel pushing 30 MPH, over the bridge above Grand Central, then down into a second tunnel-- this one a straightaway, but also slightly downhill-- on Park Avenue. Pulled all that off without incident, but...
On the way back uptown, somewhere in the 50s, I veered onto the sidewalk, which was polished like marble, and attempted to slalom between flagpoles. Leaned it over too far-- or something-- lost traction, smashed into one of the poles, destroyed the front wheel.
Was glad we had the beer, which we chugged on the way to the subway. Riding with music was never the same again. If I was in a low-traffic area or on a trail that I knew very, very well, where there was minimal risk of collision with other cyclists or vehicles, I'd consider it. So I might try it again if I ever ride in those conditions.