You're going to jail - one item with you

[Urgh76]

That Tape Recorder from that one episode of the Twighlight Zone.

That would be awesome

 

[Simriel]

a Time Vortex Manipulator. Either that or Iron Man. HE CAN CARRY ME TO FREEDOM!

 

[lee1287]

A women.

 

[Urgh76]

This. No one is making portals anywhere but me!

Spoiler

Then you find out that the jail is ENTIRELY lined with metal

 

[Sansha]

This. No one is making portals anywhere but me!

Spoiler

Then you find out that the jail is ENTIRELY lined with metal

Unless it's made of concrete walls. Which most of them are.

 

[Urgh76]

A female body guard, with big tits.

Sort of like this chick from South Park?

Spoiler

 

[Urgh76]

This. No one is making portals anywhere but me!

Spoiler

Then you find out that the jail is ENTIRELY lined with metal

Unless it's made of concrete walls. Which most of them are.

Whatever, whichever one the portal gun couldnt shoot on is what i meant

 

[seanmcdow]

one of my yoyos.
or the piano

 

[Michailov]

Deck of cards or a violin.

 

[CrashBang]

One big ass box filled with Lego.

I'll keep myself busy and happy for quite some time.

You, sir, are nothing short of a genius

 

[Sansha]

A female body guard, with big tits.

Sort of like this chick from South Park?

Spoiler

AWESOME

ROCKING

TITS

 

[superbatranger]

This. No one is making portals anywhere but me!

Spoiler

I think that right there defeats the purpose of a life sentence. Better hope I don't steal it. But if that fails, I'll have my Zune. 2000 songs, 3 movies, internet, Project Gotham Racing, and Audiosurf.

 

[Not-here-anymore]

My bow, assuming I'm also allowed arrows. Modern bows aren't designed explicitly to harm people, but it's still intimidating, being a large weapon type thing. Plus I could get some more archery practice done whilst I'm there.

Or a big-ass box of lego, but someone already said that. And I assume this is different to desert island scenarios in that you're not alone, you're in a confined space with a large number of presumably unfriendly individuals?

 

[camokkid]

Maybe an Ever-last Chasity Belt like in Robin Hood: Men in Tights?

But what if Robin Hood is there, and he's gotten a bit, erm, "desperate"?

 

[Worgen]

this about sums up what I would want

flying fucken tank

I wouldnt escape with it, Id just fly it around the yard and sleep with it

 

[TheLaofKazi]

An acoustic guitar.

As long as I can get new strings when they break.

 

[RamirezDoEverything]

A laptop(with the charger plugged into it)

 

[GeorgeLopezFnarr]

(Obvious joke) Get out of jail free card

 

[GamerPhate]

This would be good.

I seriously had one of those when I turned myself in for a pot charge years ago. I presented it to the officer, which chuckled but that was the extent of it. The funny thing is that they have to log the items you have on you when taken in, so my Inventory Manifest for release had listed:

One Get of Jail Free Monopoly Card

Which I got when I was let out.. so yeah its great for a giggle.. but sadly it doesn't work...

(also.. the OP said it can't be an item to help you escape but its all good)