The Elder Scrolls + EarthBound (Should take TES into a present-day setting, since the EB games are set in the present)
The Elder Scrolls + The Sims (oh wait, perhaps The Sims Medieval is this already

)
Super Mario Bros Crossover + Abobo's Big Adventure (8-bit NES nostalgia to the max!

)
Tim (aka the Slipperman)