EDIT: opps, I didn't read the part about five items..
Ok my five items are: my tomahawk, my .22 with ammo, a bic lighter, a small knife, and a heavy field jacket.
MY ORIGINAL POST:
For fourwheeling/wondering the woods in the greater NW, in my Jeep I bring:
1 Dual Fuel camp stove
1 Dual Fuel lantern
2 cans of soup
2 cans of ravioli
3 Gal water
2 Gal gasoline
3 cup noodles
1 4" knife, fully serrated
1 7" knife, non serrated
1 Tomahawk
1 4lb sledgehammer
1 claw hammer
1 camp axe
1 camo net large enough to cover the entire Jeep
1 tarp
1 Sleeping Bag
3 signal flares
1 high CFM 12v air compressor
2 MRE's
1 shovel
1 machete
1 first aid kit
1 3D cell LED maglite with extra batteries
1 storm whistle
5 bic lighters
1 M65 field jacket
1 roll duct tape
1 pair of jumper cables
1 recover strap
1 four sided tire iron (good for helping others as well)
1 set of socket wrenches/screwdrivers
1 torque wrench
2 pairs of extra socks
2 pairs of underwear
2 undershirts
1 pair of extra boots
1 roll of duct tape
100ft of nylon rope
100ft of paracord
1 box of tampons (for bloody noses only)
1 tire patching kit
1 road cone
1 slingshot
1 deactivated cell phone with car charger (only good for dialing 911)
1 CB radio with PA horn installed
1 set, sway bar disconnects
1 bottle of brake fluid
6 spare U-bolts for axles
1 jug of coolant
2 bottles motor oil
1 spare rear axle shaft (only if wheeling)
2 boxes .22lr
5 boxes 7.62x39
1 box .380
1 box 9mm
1 shotgun bandoleer with buck/bird/slug shells
1 12ga shotgun
If exploring new territory, I also bring my 14" bar Stihl chainsaw and an extra gallon of bar oil and 2stroke fuel for blown down trees that often cover my trail.
Don't forget to bring non perishable food!! Starvation is a miserable situation to be in!!