Forty-six years ago today, Bob Dylan played his third straight Newport Folk Festival. Leading a group comprising members of the Paul Butterfield Blues Band, as well as organist Al Kooper, Dylan strapped on a Strat and served up a three-song electric set, the centerpiece of which was his just-released single “Like a Rolling Stone.” Dylan’s noisy performance drew a smattering of boos—either because folk purists resented him for “going electric,” as legend has it, or because one of the festival’s headliners had dared to play a mere 15 minutes, as Kooper maintains.

Regardless of what actually happened, everyone agrees that 1965 marked a major turning point for Dylan—and indeed, popular music. While the electric switcheroo led to two of Dylan’s finest albums, Highway 61 Revisited and Blonde on Blonde, mid-career change-ups are risky business, and few artists fare as well. Consider the following five case studies. Some were triumphs, some were fiascoes, and others fall somewhere in between.

1. Weezer’s Pinkerton

Weezer’s 1994 debut, the so-called “Blue Album,” wasn’t without emotional heft, but the band offset the heavy stuff with geeky lyrics and a silly Happy Days-inspired video for the breakout single “Buddy Holly.” On the group’s 1996 sophomore effort, tortured frontman and then-recent Harvard enrollee Rivers Cuomo opened up about heartbreaks, insecurities, and his fondness for Japanese girls, crafting a record that -- though not without its light moments -- was more raw and visceral than some fans were ready for. But the world eventually caught up, and in the years that followed, Pinkerton amassed a cult following, inspiring a generation of emo bands. Given Weezer’s subsequent left turns, most critics cite Pinkerton as the band’s masterpiece, even if it begat a whole lot of whiny, humorless imitations.

2. Christina becomes Xtina

On her 1999 self-titled debut, Christina Aguliera played it safe, teasing listeners with such mildly suggestive lines as, “I’m your genie in a bottle/ gotta rub me the right way.” By 2002’s Stripped, Aguilera had resolved to unleash her inner-freak -- a facet of her personality so powerful that it necessitated the creation of an alter ego: Xtina. Stripped was a raunchy record, and the David LaChapelle-directed video for lead single “Dirrty” found the former Mickey Mouse Club star engaging in foxy boxing and hanging with members of the fetish community, all the while rocking assless chaps. Critics accused her of going too far, and while she later tried out new images -- retro pin-up girl on 2006’s better-reviewed Back to Basics and cyborg hottie on last year’s disappointing Bionic -- she’ll always be Xtina to some people.

3. Macca plays Fireman

Paul McCartney has collaborated with some talented people over the years -- John Lennon, Michael Jackson, etc. -- but none have inspired him quite like Martin Glover, AKA Youth. The Killing Joke founder and acclaimed producer started working with Macca in the ‘90s, and after two albums of ambient music, the pair released Electric Arguments in 2008. Featuring 13 tracks -- each written in recorded in a single day -- the collection combined Youth’s eclecticism with Sir Paul’s melodic sensibilities, proving that the architect behind some of the Beatles’ more adventurous projects hadn’t completely lost interest in experimental music.

4. Liz Phair exiles herself in Popville

Following a trio of well-received records for Matador, Phair bid the indie scene adieu and linked up with Capitol for her self-titled fourth album. She also signed on to work with The Matrix -- the songwriting team behind hits for Avril Lavigne, Britney Spears, and Hillary Duff, among other pop starlets -- and that’s where the trouble began. The single “Why Can’t I?” became a Top 40 hit, but critics were merciless, trashing the album and branding Phair a sellout. Eight years on, she’s yet to fully recover from the flogging.

5. Neil Young goes Electronic

Like Dylan, Young has changed direction so many times that it’s better to assess his catalog in total than to scrutinize every stylistic curveball. That said, the 1982 electro-pop album Trans -- released a year before another leftfield genre exercise, the neo-rockabilly curio Everybody’s Rockin’ -- remains a head-scratcher. On such songs as “Computer Age,” “Transformer Man,” and “Computer Cowboy (AKA Syscrusher),” Young screws around with synths and sings through a vocoder, presenting a chilling look at a dystopian future where talent songwriters pretend to be robots.