I found this list on Blender.com via NPR, here are the ones that stood out to me, to see all 20 check out the link:
Something’s Happening, But You Don’t Know What It Is
#7 Music publisher gives away Bob Dylan
In the early 1960s Leeds/Duchess was a legendary music-publishing company but far from the hippest: It knew Tin Pan Alley but couldn’t find a Greenwich Village coffeehouse with a compass. Yet when Columbia signed Bob Dylan in 1961, they steered him to Leeds, where he happily signed a publishing deal with a $1,000 advance. The following year, Dylan’s new manager, Albert Grossman, got out of the deal with the disinterested publisher simply by repaying the $1,000. Dylan’s new publisher, the savvier M. Witmark & Sons, received 237 songs—many of them future standards worth tens of millions of dollars—in just the first three years.
Unintended consequence The receptionists at Leeds/Duchess never have to field calls asking what “All Along the Watchtower” is really about.
Detroit At a Discount
#3 Motown sells for a pittance
In 1988 Berry Gordy Jr., reportedly losing millions of dollars on the label he had founded decades earlier, sold Motown and its incomparable back catalogue to MCA and investment company Boston Ventures for $60 million. How bad was that price? The next year, Herb Alpert and Jerry Moss sold their A&M Records to PolyGram for roughly $500 million. In 1990, David Geffen got about $700 million for Geffen Records and in ’92, Richard Branson unloaded Virgin Records to EMI for $960 million. And five years after buying Motown, Boston Ventures cashed out, selling the label to PolyGram for $325 million—a return of more than 500 percent.
Unintended consequence The Motown Atlantic airline, and Berry’s career as a trans-global balloonist, have yet to materialize.
Tomorrow Never Knows
#2 Decca Records A&R exec tells Fab Four, “No, thanks”
Dick Rowe was not the only record-label executive who passed on the Beatles in the early ’60s, but he was the only one who brushed off their manager, Brian Epstein, with the astute prediction that: “Groups with guitars are on their way out.” Epstein begged Rowe to reconsider, so Rowe hopped a train to Liverpool to check out the band live. When he arrived at the Cavern, he found a mob of kids trying to force their way into the club in the pouring rain. Annoyed, he smoked a cigarette, went home and signed Brian Poole and the Tremeloes instead.
Unintended consequence The Monkees
THE BIGGEST RECORD-COMPANY SCREWUP OF ALL TIME
#1 Major labels squash Napster
Shawn Fanning’s file-sharing service attracted tens of millions of users, but instead of trying to find a way to capitalize on it, the Recording Industry Association of America rejected Napster’s billion-dollar settlement offer and sued it out of existence in 2001. Napster’s users didn’t just disappear. They scattered to hundreds of alternative systems—and new technology has stayed three steps ahead of the music business ever since. The labels’ campaign to stop their music from being acquired for free across the Internet has been like trying to cork a hurricane—upward of a billion files are swapped every month on peer-to-peer networks. Since Napster closed, “there’s been no decline in the rate of online piracy,” says Eric Garland of media analysts BigChampagne, who logged users of son-of-Napster peer-to-peer networks more than doubling between 2002 and 2007. And that figure doubles again if you count BitTorrent.
Unintended consequence Your grandmother deciding to trade up from that dial-up connection