Last Song on the Radio

It was the last song on the radio, the last song I heard before heading off on the morning ride, the one that would last for the duration.

Why did it have to be I Shot the Sheriff?

In between replays, the back and forth banter, the left-side / right-side debate in the old noggin' over merits and detractions, was entertaining for a while. Eventually, though, it became as worn as the grooves on my old overplayed 45rpm pressed disc (which has not been played in more than thirty years).

By the way that would be Clapton's version of the song. Just to clarify.

If you ride only with groups and forgo the solo spin, you may not know what I am talking about. Each, the group or the solo, are unique monsters. Group rides require more focus, not to mention that those others in the group are there to talk and talk to. I don't think I have ever done a group ride where a song casually pops into my head and replays for mile after mile. On the other side, something needs to occupy those miles during solo rides, and more often than not, that something tends to be the last song on the radio.

"Freedom came my way one day
And I started out of town…"

All good rides start in similar fashion, don't they - "freedom", I mean, and starting "out of town". The thing is, at what point, at what mile, what replaying of the song, does that freedom become a sort of mental prison? In other words how many times does it take for  "the bucket [to go] to the well, [before] the bottom drop[s] out?"

If you can answer that question, try the bonus: What song is on the flip side?