How about John Romero failing to make anyone his bitch?

I wonder if he's married... because if he is, she obviously doesn't know about his magazine ads.

I mean no offense but your philosophy as regards art sounds strange to me.
Taking into account the hours you spend on a painting (along with the cost of paint, brushes and whatever) has nothing to do with how much you can sell it. That's my opinion.
I think about your question. ;)

Actually it's a pretty major part of it. It's called calculating a break-even point.
I know some people think it's unromantic to consider money and art at the same time, but it's a fact of the business. If you can't bring your hourly rate to a viable level, you can't make a living from art.

Minsc and Boo! (may not be very iconic to those who hasn't played BG 1 or 2, but they'll just have to live with it)

paint a grue
also, I would think painting video game characters that the player never actually got to see would be cool too. sure they wouldn't be instantly recognizeable but interesting never the less.
you could paint standard characters from Quake 3 (any FPS player worth his salt knows those) or maybe paint a highway that looks kind of like the one from audiosurf

I agree with whoever said it above (I'm too lazy to go back a page), you may want to think about avoiding like-for-like reproductions as copyright people may get on your back.
Otherwise, I would recommend taking something iconic from a game, a particular scene or object, and then putting your own twist upon it, for example, that famous fruit in a bowl still life but instead of fruit you have various gaming objects (like the cube from #1).
Oh and surely painting is done for the love of it, with money secondary?

Of course. But there's a big difference between 'money secondary' and 'money not at all.'
Romulus' logic just makes perfect sense to me. He knows he can't sell these for more than 30 pounds, so spending more than 30 pounds worth of time is something to avoid.

Whao! This thread has exploded with comments, sorry I've not gotten back to you all earlier! Thank you for all your suggestions, I've saved pretty much all of the picture references you guys linked, they're all great ideas. I think I'll produce some more and post them.
Copyright and legality for this situation isn't an issue at all. I can disclaim the lot of it to its rightful owners, not to mention this whole thing is very small scale and really no one is going to notice.
This is true, this is just a personal side project, I actually work at two jobs and have been doing this in my spare time (what is left of it).Speaking of the costs, because a few people have mentioned it, the price is up in the air. I have to make a judgement call based upon how long each one took weighed against how much I think my time is worth. I have been doing it for the love, I really enjoy it, but to sell the Companion Cube for £10 would be saddening (It took a stupid amount of hours, something like 9 or 10). Realistically the prices should be astronomical because I have been taught by my arts education to overprice my work. I simply refuse to because I want people to enjoy it and not pay through the nose.
One thing I forgot to stress; I want a buyer to feel like they got something unique as I won't be repeating the paintings. Each one is one copy alone. I thought that would make the buyer feel more respected, instead of getting a mass-produced piece.
Thank you! I don't know, I love painting these things and I'm defiantly going to do more thanks to all your encouragement.
Hell, maybe I can do a GOG Logo all nicely blended. I'm really sure it'll be DRM free... and cheap!

I like the idea of painting the Mario hat. I personally wouldn't buy a painting of any of the pixel characters. I've seen the exact pictures before. With the Mario hat, you could take just about any similar hat for a reference and pictures from the internet (I would think...but I'm no artist). You could still add a new angle or give a certain style or something. Something that would really make it your own, you know?
You could do that with the Blue Shell of Mario Kart, or the Donkey Kong barrel, or plasma rifle of Halo, or the companion cube! I like the idea of taking memorable objects from games.
I'm always fond of game inspired art that's done in a wholly different artistic way or with a neat spin on it. I'll attach few pictures. The links should take your to the artists' galleries.
The 1st is by Lemm and it's of Evil the Cat from Earthworm Jim: [url]http://rocketworm.com/[/url]
The second is by Orioto: [url]http://orioto.deviantart.com/[/url]
The 3rd is by Sean Clarity is from Excite Bike: [url]http://www.fnaok.com/index.cfm[/url]
The next pic was too big to upload, so here's a link to it. It's by Greg Simkins:
[url=]http://www.iam8bit.net/images/Simkins_Greg%20-%20Pac-Man%20in%20Hospice%20(acrylic%20on%20canvas)%2024x18%20-%20300dpi.jpg[/url]
Gallery: [url]http://www.imscared.com/gallery/[/url]
All of these seem very time consuming however. But you could apply your own style to a singular object or character rather than a landscape (like the Mario hat). Bob-omb or a Goomba would be a cool character, and they seem like they'd be fairly simple.
I hope my post wasn't too erratic!

you could do a painting of a nuka cola bottle, also, you could do one of a crowbar, or perhaps "quad damage" or maybe a breakdancer getting hit with a news paper, ala Papaerboy

First, if it were me, I agree with some other people that I probably wouldn't buy the pixel paintings at 30 pounds. At that price ($40 USD?) I'd require some level of complexity.
I recommend:
Shodan's face/ System Shock 2's cover art.
A Chozo Statue
This awesome Metroid II poster I once had
How about a Zelda overworld map?
Or this one?
This scene from Chrono Trigger is "iconic" imo
Another good one

it must have been a while for me, because I don't remember either of those!