5 - Pitfall! (Atari 2600)
I have fond memories of playing this game obsessively because if you sent in a snapshot of the elusive "gold bar" to Activision, you would receive a Pitfall! poster.
I don't remember what the poster looked like, but the box for this game was magnificent:
What's great about this box (besides the rainbow coming out of the protagonist's back) is that it is truth in advertising. What you're looking at on that box is the entire game. Go from one screen to the next and you will see the same thing over, and over, and over again. That kind of audacity is just not something you see in video games anymore with people requiring things like plot and context and endings.
4 - Rygar (NES)
I debated putting this on the list because I don't know that any game brought me closer to tears of frustration more often than Rygar. But I kept playing it anyway because there was something hypnotic about just bashing things with a flaming yo-yo.
That's right, a flaming yo-yo.
Look at how bad ass this dude is. He is vaulting over what looks like some orc while wielding his yo-yo.
Actually my brothers were much better at this game than me (not surprising since my brothers are better at everything than me). I remember marathon sessions of this game because unbelievably, there was no save or password feature despite the game's absurd length. So basically you'd have to break for lunch and possibly dinner to have any hope of getting to the end. It's that kind of "screw you" to the player that makes this one a classic.
Hardcore Gaming 101 has a detailed analysis of Rygar, if you'd like to learn more about the game's historical significance (which I still believe can be summarized simply with "flaming yo-yo").
3 - Castlevania: Symphony of the Night (PS1)
The Castlevania games are probably the best platforming series out there (with apologies to Mario and Mega Man), and Symphony of the Night is still the best of the bunch.
The game introduced a leveling up concept to the series, and as World of Warcraft has ably demonstrated, there is nothing more addicting than leveling up. Add to that the fact that when you complete 100% of the game, you discover that there is an additional 100% of content you need to finish, and you're locked in for awhile.
A lot of what puts these games on my lists has to do with fond memories, and I remember visiting my buddy Jay in the Bronx one weekend during college. We played this game for about 48 hours straight while rotating turns at the controller. Anything that inspires that level of insanity has to be good, right? Now based on that logic go out and buy yourself some crack.
2 - Contra (NES)
Up Up Down Down Left Right Left Right B A Start.
1 - Cave Story (Doukutsu Monogatari) (PC)
I'm going to be accused of being obnoxious for putting an independently made, lesser known, free game as my #1 choice, but I'm telling you it deserves it.
Cave Story has a surprisingly complex plot, terrific gameplay, a wonderful cast of characters, and you can download it free on PC or Mac. When thinking about this list and this game I had to go fire it up again and it is just as awesome as ever.
I mean c'mon, the main character's name is "Quote" and the female friend is named "Curly Brace", you know you're in for something original.
Go try it now.
Worst Ever - Captain Novolin (SNES)
Many attempts have been made to make video games educational tools. Some of them have succeeded. Captain Novolin is the Hindenburg.
The game was targeted towards kids with diabetes to help teach them about taking insulin and staying away from sweets. Actually playing the game however teaches you nothing but a desire to throw oneself out of the highest available window to end the pain.
Fast forward a couple minutes in to see actual gameplay. The controls are so bad that it is difficult to avoid actually getting hit by the enemies (such as the evil bouncing donut), and you have no obvious means of attack to aid your chances of survival. Imagine if you're a kid with diabetes and you're thinking "Hey, this superhero has diabetes, it can't be all bad." Then you play this game. If I saw a box of Dunkin' Donuts after playing this mess for a couple of hours I would just curl up into the fetal position.
See The Philosophy of Time Travel's completely wrong choice for worst game ever here.
See LastBestAngryMan get so angry he refuses to even name a top five here.