I came up with a Top 20 list on another answer, and here's what I suggested. All of these are very useful in their own way:

Here's a list of things I think are must-haves:

1. Twitterfon (a Twitter client that I think is better than Twitterrific)
2. Mint (from Mint.com, a personal finance tracking site)
3. Google (includes google maps, reader, mail, etc)
4. Lockbox (a password keeper--I use so many passwords it's necessary for me)
5. Facebook (just a necessity)
6. Crosswords, or Crosswords Lite for a free version (kills time everywhere)
7. Yelp (whenever I'm out, I look around for restaurants and reviews
8. Tap Tap Revenge (again, good way to kill time)
9. Pandora (Internet radio at its best)
10. Fring (the best IM client I've seen)
11. Shazam (if you're listening to music, you hold this up to the speaker and it will tell you what the song is. Very cool).
12. Galcon (kind of a space-based risk game. I just enjoy it)
13. Google Earth (just awesome)
14. i.TV (a TV guide app. Useful)
15. SmartRSS (the best RSS reader for the phone I have found)
16. Remote (allows you to control your computer's iTunes from your phone. Great for hosting parties)
17. Youtube (of course)
18. Lightsaber app (just because being a nerd is always awesome)
19. Weatherbug (much better than built-in weather app)
20. NYTimes (gotta stay informed)

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