I'm sure you've seen it before. The "what X would you take if you were stuck on a desert island?" or "What X would you Y if that was the only thing you could Y?" Or something of the sort. Those silly, annoying questions that ask you to pick a few things, not even considering the fact that picking a favourite X may cause you great emotional distress, turmoil and mental unrest and ARRGRGHRGHH...
Sorry about that.
Still, they are interesting sometimes. Trying to think of article subjects the other day, this one was a potential topic. Instead, I went with the fruitless "hidden music track" quest. That quest showed me one thing - my Dreamcast collection is surprisingly small. This top 5 would represent almost 1/4 of my collection of 23 games! Fortunately, this is a hypothetical scenario, so I can give myself all the Dreamcast games, even the unreleased ones. I could even give myself a Dreamcast 2!
Deciding this list depends solely on one thing: replayability. (Or replay value, if you want to be a hater.) Can I play this game many times without getting bored? Can I learn speed-running techniques to learn and master the game? Can I find some wicked glitches to totally break the game? Also, soundtracks are an important consideration. Despite this, it's still rather difficult to imagine that scenario, given that I have over a dozen systems plus a robust emulator on my Mac.
So, in no particular order, here we go: