Now that jailbreaking an iPhone is as simple as visiting the right website, it’s hard not to want to tread into the exotic, somewhat sketchy seeming world of jailbreak apps. But what can you get from the grey market that you can’t get from Apple’s bright and shiny App Store? Just plenty.

Need to justify your switch to the dark side before you throw that ominous jailbreak slider? Take a look at some of our personal favorites.

Also check out our picks for the best iPhone apps approved by Apple.

 

RockApp, Free through Cydia

When you jailbreak using the latest exploit – Jailbreakme.com – you only get one third-party app store installed: Cydia. RockApp is basically the Ford to Cydia’s General Motors, doing much the same thing, but a little different. It contains a lot of software you simply can’t get from Cydia, and even has what we consider a better interface. Apps typically cost more money, but every single one comes with a free trial, so you can make sure it’s worth purchasing before breaking out the credit card.

 

MyWi 4.0, $19.99 on RockApp

Use your iPhone’s wireless connectivity on your laptop without paying your service provider a dime. MyWi works with both Wi-Fi and USB, though we actually recommend the latter because tethering drains the battery so quickly. Unlike some alternatives, it also requires no desktop client: Just connect the cable, let the app work its magic, and you’re online wherever you have cell signal. Unfortunately, the app costs $19.99–ten dollars more than it did originally. However, this one-time charge is tiny in comparison to all the monthly fees you’d likely pay your wireless carrier for tethering capabilities. 

 

nes4iPhone, $4.99 on RockApp

Relive the glory days of the original Nintendo with this polished NES emulator for the iPhone. The virtual controls can’t quite match the red and black buttons you mashed back in ‘89, but we figure having every NES game ever made in your pocket more or less makes up for it. Granted, it doesn’t actually come with any ROMs, but crafty, subversive types (like those who jailbreak phones in the first place) will quickly figure out how to load their phone with them for free. Even your snotty rich friend with arcade games in his basement never had that much entertainment stockpiled in his closet – much less in his pocket.

 

My3G, $3.99 on RockApp

Like its sibling MyWi, My3G lets you contort AT&T’s 3G connection in ways AT&T never intended. More specifically, you can run apps that are supposed to only have certain features over Wi-Fi networks, like FaceTime, over 3G networks. Video streaming performance obviously suffers, so your results may vary, but a free trial will give you plenty of time to make up your mind.

 

Winterboard, Free on RockApp

Don’t care for the iPhone’s tasteful but bland home screen? Winterboard lets you reskin every aspect, including custom icons for apps, or choose from the hundreds of themes that artists have already cooked up.

 

Bite SMS, Free with ads or $8.99 without ads on Cydia

Composing and responding to messages with iPhone’s native messaging app is pretty easy, but if you’d like it to be even easier, check out Bite SMS. In addition to saving you time by allowing you to quick reply directly from a message’s pop up alert, the app features a host of other useful features such as quick compose, scheduled messages, auto-forward, auto-retry, passcode lock, and much more.

Bite SMS Jailbreak App 

Zephyr, $4.99 on Cydia

 Despite iOS’s generally easy-to-use interface, multitasking on the iPhone can sometimes be a pain. If double-clicking the home button every time you want to switch apps feels clunky and inefficient to you, then check out Zephyr. Once installed, the app will allow you to multitask the way you’ve always wanted to -– by using single-finger gesture controls. It’s pretty simple to use; swipe up from the bottom of the screen to activate the app switcher, and swipe side-to-side to jump between recently used apps.

Zephyr Jailbreak App

 

iDiscrete, $2.49 on RockApp

Friends grilling you about some of the photos and video they dug up on your iPhone after you passed it with it in your hands after your 76th game of Solitaire? It’s OK, we dress up our dogs and make them play house, too. IDiscrete not only allows you to hide your secret files behind a password, it blends in so well that the casual inspector of your phone won’t even know you have anything to hide. The “password” is actually a series of strategic screen touches on a fake load screen, and you can even disguise the app as one of your unused Apple icons, like stocks.

 

iBlacklist, $11.99 on RockApp

It’s none of our business why you have bill collectors, exes and inebriated friends calling you at all the wrong times, but iBlacklist is here to help, not to judge. As the name implies, it can blacklist certain numbers, but also do a whole lot more. You can whitelist the people you do want to access your phone for stricter control, choose one of four actions (from hang-ups to busy signals and send to voicemail) for blocked callers, and even schedule which times, or even days of the week, to apply different types of blocking.

 

FastSnap, $0.99 on RockApp

Oh, how we wished Steve Jobs would concede to the power of the button and endow the iPhone 4 with a hard shutter button for the camera. No dice. But those volume buttons will double for them nicely with FastSnap, which lets you use either the up or down volume button to trigger the camera. Brilliant! File this one in the why-didn’t-Apple-think-of-that category.

 

This article has been updated to include software updates, price changes, new apps worthy of being labeled the best jailbreak apps, and more.