Singer-songwriter Steve Earle pops up here and there in all five seasons of The Wire. Half way through the first season, he makes the first of several appearances as Walon, a recovering addict and a Narcotics Anonymous mentor and sponsor to one of the series' major characters. At the end of the second season, Earle's song "Feel Alright" is the prominent backdrop for the season-capping montage. (Every season ends with one; the one that closes the season about blue-collar dock workers belongs to Earle.) And in the fifth season, Earle opens every show with a cover of the Tom Waits song "Way Down in the Hole."
Jimmy McNulty: Why New York?
Omar Little: Must be something happening out there, man. Too big a town, know what I mean?
By the way, in case you missed this tweet from Darren Hughes: Alan Sepinwall is writing detailed synopses and analyses of The Wire, episode by episode. They're a great way to revisit the show. Sepinwall is churning up lots of new ideas.