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alerion26:
Warren Zevon, Dire Straits, The Clash, Billy Bragg, Rancid, Old 97s, Dropkick Murphys, Buddy Guy, Michael Hill (& his Blues Mob)… Edit to add: Had to return to add Chrissie Hynde, Cowboy Junkies, Bob Marley (of course) and, my guilty pleasure: Jimmy Buffett.Β 
alerion26:
This would be better answered by playing a "game" I learned from a girl at a pub in Malden one eveningβ€”you exchange iPods (obviously this was a few years back) as an icebreaker. I thought it was brilliant.Β