Update 5/17: Updated apps
Update 1/21: Based on latest apps I used on my iPhone5 and my recent 18 day “trial” of the great HTX 8X Windows Phone 8. But WP8 was lacking too many apps and some of the ones it did haven’t weren’t nearly as good as the iOS version. See this post for more details: https://blog.jasonsherry.net/2013/01/08/returning-my-windows-8-phone/

Social Media

Facebook – Duh (Much better on iOS than Android and WP8)
FourSquare – Find local places, see & leave tips from others, check out pics of places, and become the “mayor” of them (WP8 version is sexier, but missing a few features)
GetClue – Used to track, chat about, and get “stickers” for TV shows & movies you watch
GroupMe – Group SMS\txt app, works off SMS alone but App makes it better
Twitter – Required for iOS5 integration and always has the latest functionality
TweetCaster – Great for filtering\hiding post to get rid of the noise on Twitter
Latitude – My GF, her oldest kids, and a few friends  use it all to see  where each other are at

My Data

OurGroceries – Used across my phone, GF’s, and assistant to track anything we need from the store
OneNote – Note, list, etc app that lets you share notebooks with multiple users (iPhone, Android, Windows Phone, PC, Mac, and most browsers)
Carrot  – To Do track, used just for the critical things I need to do daily or soon
SkyDrive – Access and view Office documents stored in Skydrive.com
Sleep Cycle – Sleep tracking app
2Do – To Do tracking app, used across my GF’s and my phone. Mainly used for tracking thing that we want fixed\done around the house
Workouts – Lots of exercise programs
Norton IDSafe – Allow access to all my username and password, can access from PC to using Norton Internet Security

Travel

Waze – Social media traffic app, share traffic speeds, police traps, accidents, bad traffic, etc (This was my MUST have app, there is no WP8 version currently planned)
TripIt – View your travel arrangements and your friend’s, if they use TripIt.com
Orbitz – Search and book travel plans
Kayak – Search and book travel arrangements
Transit -Route using public transit data in iPhone Maps

GPS MotionX Drive – Driving GPS (Replaced by Waze)
AroundMe – Similar to above (Replaced by improvements in 4sq)
GasBuddy – Fine the cheapest gas (Replaced by feature in Waze)

Music

Spotify – Streaming music from almost every label, this is a game changer!
Remoteless – Remote control Spotify (No WP8 version)
SiriusXM – This was also a must have app that there was no WP8 version of
SongKick – Track your favorite bands, which can be imported from local music, Last.FM, or Facebook
iRemote – Remote control iTunes or MediaMonkey (No WP8 version)
LiveNation – Buy tickets
BandMate – Similar to above, but shows bands that similar to ones you already like
SoundHound – Search for song name and lyrics based on a song playing, like Shazam but it support whistling and humming a tune into and it faster!
Playmysong – Create  shared radio station that your friends  can join and add songs too
Turntable – Join and optionally DJs in rooms

Info\News\Weather

Pulse – News aggregator using categories and groupings
Flipboard – Easy browsing of news feeds on different topics, Facebook, and Tumblr
CNN
Westword – Denver area free magazine on events, music, politics, happenings, etc
IMDb – Get your movie facts
NY Times
The Weather Channel
WolframAlpha – Ask it a questions like “Highest Mountains in the US” and it will give you an answer with the data about them
Wired News UK

Photography

Microsoft Photosynth – Take 360+ degree photos
Flickr – Great if you use Flickr to store your photos (No WP8 version)
Tumblr –  Used mostly for browsing porn on my iPhone 🙂
MyDisk – Used for encrypted storage of dirty pics 😉

Entertainment

Amazon Video – Like  Netflix, this is what we use for most  of our TV watching (using the PS3, not the iPhone)
Netflix – Stream movies\shows to your phone
LG TV Remote –  Smart TV remote over WiFi
YouTube
Flixter – Find movies times and get tickets
Kindle – Read books from your Kindle collection
OpenTable – Book reservations
Dexter – Know what’s going on and who’s in what episodes
Failblog – See content from http://failblog.org
DirecTV – Control your DVR from anywhere (Canceled my DirecTV service in 10/12)

Skiing & Outdoors

Ski Tracks – GPS based tracking and stats (No WP8 version)
REI Snow Report – Snow fall reports and alerts (No WP8 version)
Snow Conditions – Similar to above (No WP8 version)
Endormondo – Track how many calories you burn while running, biking, skiing, etc (No WP8 version)
iTrailMap – Download and view ski trail maps (No WP8 version)
MotionX-GPS –Good outdoors adventuring GPS app (No WP8 version)
GoSkyWatch – Find starts, contestations, planets, and more

Finance

Amazon – This app alone will pay for your data fees every months if you shop much
Newegg – I buy all of my computer stuff from newegg.com (No WP8 version)
Mint.com – If you use mint.com to download your transactions and categorize them,  like Quicken used to do, then get this app to check on things (No WP8 version)|
Square Register  – Take credit cards
Square Wallet – Pay with Square
PayPal Here – Take credit cards
PayPal – Pay with PayPal
Tab – Take a picture of the bill, choose who ordered what, and get a total per person

Others

iLogger – Track\log anything you can think of
MagicPlan – GREAT app for quickly creating a floor plan, just stand in one spot and take pictures!
TapTyping – Touch typing trainer and game
Skype – IM and calling client

Jailbroken Apps & Tweaks

I jailbroken my iPhone 5 running 6.1.2 a in mid April ’13. It took about 5 minutes, but getting cool things working on it has taken much more time.

IntelliScreenX – Add pull-down support from locked or unlocked screen to see latest alerts, e-mail, twitter feed, news, & Facebook feed. Also added quick access to toggle WiFi, flash, Bluetooth, data, airplane mode, vibrate mode, and other things
Remote Messages – Provides web based access to get\send\read txt\mms messages from any browser on your home network
SBProfiles – Setup scheduled profiles that dim screen, turn on\off ringer, vibrate, WiFi and other things. At 11PM my phone goes silent, vibrate off, and screen dimmed to max. At 9AM it changes back to normal
Velox – Adds slide up\down pop-ups on some apps
Cydget – Added support for HTML modification of home and lock screen, which in turn can be used to display about anything on them
Original post from 6/23/2011

My phone now does most of what I used to do on the PC. I watch for upcoming concerts (Live Nation, SuperGlued, BandMate, Stub Hub), get tickets, plan for festivals (Voodoo, Bonnaroo, SSMF), plan travel(Kayak, TripIt, Orbitz, Southwest, Places, AroundMe), communicate with friends (Facebook, Twitter, FourSquare), text, e-mail; but rarely do voice), get the News, check the weather, listen to music (Wolfgang’s Vault, Pandora, iPod, SirusXM), update my notes and access by key info across multiple systems & phone (OneNote), setup dates (OkCupid, eHarmony), share\show photos (Flickr, Photosynth, camera), control my entertainment (DirecTV DVRs, iRemote, NetFlix), watch some videos (YouTube, PBS, Veno, failblog, NetFlix), find my way around and where I go (MotionX, Google Earth, SkyWatch, Waze, Google Maps), buy stuff (Amazon PriceCheck, Living Social, CraigsList, Amazon.com, NewEgg, Target)