Just bought the classic game The Ninja for the Master System for a total of £3.88 - not really a bargain because it goes for that price on average anyhow, but it's probably the cheapest I've bought one for.
Yourself?
Cheapest you have ever paid for a game?
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Bought Gleylancer Complete for 65 dollars shipped and Keio Flying Squadron Mint Complete for 95 dollars shipped on Ebay. Not cheap, but compared to what Gleylancer ($120+) and Keio ($150+) actually cost on Ebay, I think it's pretty cheap. 

"You're just given the illusion that your decisions can actually make a difference when in the end all has been decided by the programmers." NebachadnezzaR
Assuming 'free' isn't paying for... hmm...
I did get a copy of Super Street Fighter II for the SNES for 25 cents. I was working at a game store, not any of the current national shops, and we had a policy of; If the store won't buy it and an employee wants it, the employee can buy it. It's actually a good policy if you think about it. At least the customer gets something.
The cart had no label on it, which means we wouldn't take it, so I offered them a quarter. They took it.
Cheapest new game would probably be the first game I ever bought. I'm 28, so I was alive during the great video game crash. The market was flooded with crap 2600 games and stores were slashing prices to just get rid of them. I bought a copy of Pigs in Space for the 2600. I believe it was 50 cents or so, I think I was 4 years old.
One other way we can look at 'cheapest' is compared to how much people normally spend. I bought Bust-A-Groove for the PSX for $5. It goes upwards of $80 on eBay. That's probably one of the biggest margins I have.
I did get a copy of Super Street Fighter II for the SNES for 25 cents. I was working at a game store, not any of the current national shops, and we had a policy of; If the store won't buy it and an employee wants it, the employee can buy it. It's actually a good policy if you think about it. At least the customer gets something.
The cart had no label on it, which means we wouldn't take it, so I offered them a quarter. They took it.
Cheapest new game would probably be the first game I ever bought. I'm 28, so I was alive during the great video game crash. The market was flooded with crap 2600 games and stores were slashing prices to just get rid of them. I bought a copy of Pigs in Space for the 2600. I believe it was 50 cents or so, I think I was 4 years old.
One other way we can look at 'cheapest' is compared to how much people normally spend. I bought Bust-A-Groove for the PSX for $5. It goes upwards of $80 on eBay. That's probably one of the biggest margins I have.
Why do you all get better deals than me? I don't like you all anymore...
Seriously, though, I feel like I have to have my games complete and preferably in the best condition possible. So I especially don't like you anymore, Ottobot...
Just kidding. You're all cool - and cheap.
Share your bargains!
On a side note, I got Jet Set Radio Future/Sega GT 2002 bundle free with my Xbox, so that was fortunate. Shrugged off JSRF at first, but later found it to be an awesome game. I recall completing it with only around two, maybe three more extras I needed to complete... couldn't do 'em, and after I went back to do them again one day, I found some demons had ruined the disc.
Anyhow, I digress...
Seriously, though, I feel like I have to have my games complete and preferably in the best condition possible. So I especially don't like you anymore, Ottobot...
Just kidding. You're all cool - and cheap.

On a side note, I got Jet Set Radio Future/Sega GT 2002 bundle free with my Xbox, so that was fortunate. Shrugged off JSRF at first, but later found it to be an awesome game. I recall completing it with only around two, maybe three more extras I needed to complete... couldn't do 'em, and after I went back to do them again one day, I found some demons had ruined the disc.
Anyhow, I digress...