Weird Al Yankovic doesn't do albums anymore because the musical monoculture has evaporated. Even the most popular Top 40 hits exist within narrow niches nowadays, with very little overlap between fans of different genres. He says it's next to impossible to stay relevant with his parodies because by the time he's written and produced one everyone has moved on to something else. There aren't really any big summer songs that get played nationally, everyone just listens to their own curated playlists, so writing five or six parodies for an album would be an exercise in futility. He only does sporadic singles now, and that's a damn shame.
For this reason, I propose he return to his roots in the 70s, 80s, and 90s, and start parodying classic songs he never got around to back in the day. He could release a throwback album called "What Did I Miss?" to capitalize on nostalgia. Instead of chasing a moving goalpost, he can go after existing tentpoles, win-win, instant brand recognition, eternal relevancy.