You get brown underwear

I insert a quarter

You get pants.
I insert a USB drive.

You get Simmanis code.

I insert a dragon.

You get a copy of the best portrait of Skimbo ever made.

I insert an inkjet printer (with extra large ink cartridges)

You get laser printer without cartridges.

I insert Helium...

You get Carbon-12 thanks to the triple-alpha process. Because vending machines do nuclear fusion.

I insert a Canadian quarter.

You get an american penny
I insert a silver dollar

You get a taco

I insert cheese (for said taco)

you get sour cream for the same taco
i insert myself

You get a billion dollars. Too bad you're forever stuck in the vending machine.
I insert a cruise ship.

You get a vending machine, in a vending machine!

I insert barrel...

you get cracker barrel
i insert peanut

you get an elephant
I insert a picture of the elephant

You get an elephant-looking steamroller.
I insert a steamroller.

You get a new road.
I insert an emu.

you get a zoo
i insert elephant

You get elephant horns and bones (oh poor elephant )

I insert the bones again...

You get elephant.
I insert TC's emu.

You get pooped on
I insert a Cruiseliner

You get a massive brochure advertising competing cruiseliners.
I insert my own brochures advertising random stuff.

You get a good fire in the fireplace.
I insert a 7-Up.

You get Mountain Dew!
I insert a City

You get a TC Town
I insert U Drive It from SC4.

You get U Drive It from SimCity 2013
I insert hands

You get gloves!
I insert a Gaming Console