A continuation of sorts!
Musical: Hedwig and the Angry Inch
Honorable Mention: Rent
Hedwig is the only musical that I’ve seen twice in the same run. It’s one of the first musicals that I went to with my future wife, it starred Anthony Rapp in it, and it’s the primary reason that Katie works in the theatre. The songs rock, the story is funny and sad, and it’s a one-man show that never quite feels like the typical one-man show. I doubt I’ve listened to the soundtrack as much as I’ve listened to Rent, but no two live performances of Hedwig are the same; it manages to capture the absolute joy of live theatre.
Video Game: Portal
Honorable Mention: Ico
The mark of a truly great game for me is the feeling of regret that I have when I realize that I will never again get to experience it for the first time. Portal is a game where I would gladly watch someone else play it, just so I can vicariously experience it again for the first time. It is a brilliantly designed puzzle game that just happens to be controlled as if it were a FPS. It has a superb storyline and witty dialogue. The companion cube and the end credits song are already iconic in gaming canon. It’s hard to overstate my satisfaction. Portal exceeded all of my already high expectations.
Ico is a different matter. I played Ico when I was still just getting into games and it took me by complete surprise. It was the first game I ever consumed over a weekend, playing it because I didn’t want to do anything else. It’s probably the first game that showed me the emotional power that the medium was capable of.
Radio Show: This American Life
Honorable Mention: Wait Wait…Don’t Tell Me
It’s a smaller pool to pick from, as there aren’t all that many radio shows, but I’d be hard pressed to find any other 60-minute aural experience that beats This American Life. The show manages to continually find stories that are interesting and thought-provoking and I look forward to hearing each week’s podcast when I go to work on Monday. Wait Wait is a bit lighter, but it keeps me updated on major news, as well as being consistently good for a laugh. I’m not a big podcast person, but these two shows have a permanent spot on my list.
Board Game: Settlers of Catan
Honorable Mentions: Power Grid, Category 5
Neither of these are really daring picks, but in the long run, I think I’d take Settlers over other games I’ve played. It’s relatively easy to teach to new players, is a great gateway game for players who haven’t played many Eurogames before, and has a great balance between luck and skill involved. The fact that it forces direct player interaction through trading is icing. Power Grid and Category 5 are on opposite sides of Settlers; Power Grid is a bit more hardcore and Category 5 is a bit lighter. I love the critical decision-making in Power Grid, especially as decisions in earlier phases can have large impacts in later phases. And I love the tension in Category 5 as you attempt to read the minds of your fellow players just before you flip over your numbers.
I didn’t love Moulin Rouge! right away. I remember seeing it in college in our campus auditorium with several people a few years older than me (Matt Heap, Clare, and Darren maybe?) and feeling like it was a pretty solid movie. Then, I watched it again. And a few more times, with the commentary. I don’t know if it’s the perfect sad love story, the musical numbers, or the frenetic acting through most of the first half of the film, but this is a movie I’ll never turn down. It makes my lips quiver and my eyes water every time. In a very different way, Juno makes me laugh and cry and want to have a baby with Michael Cera. I mean, my wife.
Album: Ben Folds, Rockin’ the Suburbs 
TV Show (active): Lost 
Two years ago, I had never heard of a Canadian show called Slings and Arrows. Now, it’s probably my favorite show ever. Clocking in at only 18 hours of television across three 6-episode seasons, it’s something that can be watched in its entirety in a single weekend. At times funny and touching, all three seasons are constructed masterfully without a wasted minute on screen. There’s nothing to do when the final half hour of the series plays other than weep.