Ever since we "moved" downtown, Roommate has been saying that he wants to go to Howl at the Moon. In my mind, it's just a step up from karaoke, and I am no fan of karaoke. My rule of thumb about this kind of thing has always been: "would I want to date someone who I met at X?" And the answer for Howl at the Moon is "most likely no." (unless said person -- hopefully a Johnny Depp/Mike Rowe/Ira Glass/Craig Ferguson combo-- had been dragged there against his better judgement).
That being said, I can think of no better time to go to Howl at the Moon than New Years Eve: a night about spending time with good friends, not a night of trawling for hot dude action. It's pricey, but they do seem to pack a lot of stuff into the cover price.
When I lived in New Orleans, I used to be able to abide the "dueling pianos" at Pat O'Briens only when I was seriously in my cups, you know? But when I WAS in my cups, "dueling pianos" suddenly became a pretty good, fun idea... so who knows?
Pros: At $100/pp you're guaranteed seating, and that's a big deal on NYE. Open bar. Free buffet.
Cons: Uh, it's Howl at the Moon. Sorry, I'm still not sold on the "fun" quotient here. That being said, with a few of the open bar drinks under my belt, I'd probably have a great time.