Portland
From Alex's bookmarks I found Robby Russel's two-part series on Portland coffee shops and cafes: part 1 covers Costellos Travel Caffe, Urban Grind, Fireside Coffee Lodge, Redwing Coffee & Baking; part 2 reviews Pier Coffee, Backspace and Three Lions Bakery. Of the ones he reviews, I have only been to Backspace, which has video games in the back, some classic and some contemporary. He hasn't reviewed Portland Coffee House on Broadway, which has sweet wifi, eclectic music, and an interesting mix of suburbanites who get takeout and relatively less haughty regulars who stick around for a little while.
I try to go visit my friends there once a year, but it didn't work out in 2006. Things might have changed since the last time, but the next time I do go, Robby has given me some ideas for places to hang out.