VH1 actually had two series bearing the name, My Generation. The first was a video oldies show emceed by Herman's Hermits frontman Peter Noone, which had a pretty good run. In 1998, the network resurrected the title, but rebooted it as a game show, hosted by comedian Craig Shoemaker.
It's standard quiz play along the lines of, say for example, College Bowl, but with, of course, an emphasis on music. Unfortunately, viewers weren't digging, and the show was cancelled in short order. VH1 would replace it with Rock & Roll Jeopardy!, spun off from a certain quiz show franchise that's still going strong today, though the Rock & Roll version only lasted a couple of years, and was previously reviewed.
Let's take a look at a sample compilation of My Generation in its quiz show itineration.