1. What If The Beatles Never Broke Up? As much as we like to think of the Beatles dissolution as a tragedy, it was probably the best option for everyone involved. They had begun to resent each other, and everyone (especially John and Paul) was stifling the creative process of everyone else. That's what happens when you have multiple geniuses in the same band; they're both going to want total creative control and they're going to spend a lot fo time butting heads. By splitting him, the beatles thrived as solo artists, and they made the masterpieces they wouldn't have been able to make if they had stayed together. My guess is, if they had stayed together, we would've still gotten some great albums, and some of the best solo Beatles songs would've made those albums, but the overall body of work wouldn't be as impressive as what we have now.
2. What if Kurt Cobain never commits suicide? Yeah, it's a spooky one, but come on, you've thought about. One thing that was clear from listening to In Utero, was that Cobain wanted to be as non-commercial as possible. He hated all the mainstream fans who had latched onto Nirvana when "Smells Like Teen Spirit" became a smash, and he wanted to shake them off as quickly as possible, so he made a very diificult, but ultimately rewarding third album. My guess is, if Kurt had lived, he would've continued going further in that direction. The few radio friendly singles of In Utero would've been gone in favor of more brutal, uncompromising work. A fourth Nirvana album likely would've been very experimental, and gotten rave reviews from critics, but it wouldn't have found much of an audience.. and Cobain would've been thrilled.
3. What if The Replacements had gotten huge? The beloved Minnesota indie-rockers might be the most famous "should've been huge" band ever, and listening to their output, it's hard not to disagree with that sentiment. Albums like Tim and Pleased To Meet Me are filled with tracks that should've been huge hits, but somehow it never happened, as the band only scored one minor hit with 1989's "I'll Be You." But suppose they had gotten big? I think they would've handled it pretty well. Unlike Cobain, Westerberg didn't cling to the romantic notion of being an underground artist. He was okay with not being huge, but he woukd've loved being huge just as well. If Tim, their first really, really accessible album had broken through, they probably would've been one of the bigger bands of the late 80s. You could picture Westerberg's undeniable hooks bridging the gap between alternative rock, and mainstream rock, and the Mats would've had the breakout that Nirvana did, and they migth have been better suited to handle it. Then again, they were notorious drunks, and they probably would've had some onstage meltdowns that would make Billie Joe's recent meltdown look like child's play.