It was the best of times, except when it got really awkward. For all its limitless potential of uplifting the human spirit to a more enlightened state, the music world is not immune to controversy, scandal, and downright cringey awkwardness. While some incidents go on to forever populate the internet as memes, others leave long-lasting marks on essential aspects of making, sharing, and enjoying music. Let’s briefly revisit some of the most memorable controversies and awkward moments in music, to date. 

Thou Shalt Not Lip Sync

It’s difficult to not think about how certain seemingly small choices in performance, such as when not to lip sync, ended up causing notable and lasting ripple effects. 

One relatively recent such instance was Ashlee Simpson’s gig as musical guest on Saturday Night Live in 2004. While promoting her freshly released album Autobiography, the rising star of the Simpson family was unpleasantly surprised when the vocal track that started playing was all too visibly not what she had prepared to sync with. The show being, well, live, everything went downhill from there. From the awkward dance walk off the stage, to blaming confusion on the band at the end of the show, and then throwing it to a bad case of gastric disorder, the hole she kept deepening would prove impossible to come out of. 

The most notorious lip-sync case, however, remains producer Frank Farian’s experiment, Milli Vanilli. The German-French pop-duo was brought on to serve as public faces for singers Charles Shaw, John Davis, and Brad Howell, whom, although talented musicians, Farian thought they lacked a marketable image. This would turn out to be a pattern that Farian would employ several times. The extra stir regarding Milli Vanilli, though, stemmed from the fact that in 1990, the group were nominated for and won the Grammy for Best New Artist. When it was confirmed publicly that neither of the two men understood to constitute the group had actually ever performed any vocals during recording sessions or in any of their live performances, that Grammy became the only one ever to be revoked. 

Thou Shalt Not Snub

It seems that, no matter how hard the Academy tries to achieve harmony with mainstream sentiment regarding musical achievement, there will always be plenty to contest about each edition. Sometimes you snub the Grammys, and other times the Grammys snub you. Or they haven’t figured you out yet. One thing is certain: the 62 Recording Academy award ceremonies so far have yielded several unflattering moments that live rent-free in many of our minds, to this day. 

Before rapper Kanye West took it upon himself to correct the judging of Best Female Video during Taylor Swift’s acceptance speech at the MTV Video Music Awards in 2009, the late Russell Tyrone Jones (a.k.a. Ol’ Dirty Bastard) stood up for Wu Tang Clan’s merits at the 1998 Grammys, just as Shawn Colvin was stepping up to the microphone to accept the award for Song of the Year. 

Although there are always disputes regarding who should have won the Grammy in the Best New Artist category, sometimes it does seem like the Academy lacks proper understanding of some of the emerging music genres. For example, the first year that the Recording Academy recognized Hard Rock/Metal in its own category, the voting members gave the inaugural Grammy for Best Hard Rock/Metal Performance Vocal or Instrumental to British band Jethro Tull, when Metallica was nominated for its fourth studio album, “… And Justice for All.” Or that time in 1993 that the Grammy for Best Rock Song went to Eric Clapton’s “Layla” (unplugged) over Nirvana’s Smells Like Teen Spirit. 

Pope’s Nopes

Quite a few controversial incidents caused a stir to high heaven over the years, or at least to the highest of ranks within the Catholic Church, eliciting comments from the Pope himself. 

One such episode that comes to mind could be boiled down to a case of “same language, different funny bones,” except it very much wasn’t. In 1966, during a candid interview with Maureen Cleave for the London Evening Standard, John Lennon made the famous “we’re more popular than Jesus” remarks. While pretty much nobody in England took any notice of the 25-year old’s offhand comments, matters unfolded quite differently in the United States, where the interview was syndicated several months later. Reactions included banning the Beatles’ music from being played on the radio; on-air destruction of physical copies of their albums; the end of the band’s touring career; “eternal damnation” of their songs by religious leaders across the Bible Belt at the time; and even a Papal denunciation of Lennon’s comments, in a statement to the Vatican newspaper. 

Another example of Vatican-level upset in music happened in 1989, when the world received the video for Madonna’s hit song “Like a Prayer.” While the musical blend of gospel with the singer’s more usual dance-pop expression marked a notable shift in style for the artist, the music video pushed enough buttons to draw attention toward very different topics. Conservative America was deeply irked by the video’s depiction of racial and religious imagery. Italy banned the video from being shown on state television.

The Vatican condemned the choice of use of Christian imagery and called for a boycott of Pepsi after one of the brand’s commercials featured the song. Madonna’s contract with Pepsi, having only recently been signed, was cancelled. Pope John Paul II even flat-out called for a boycott of Madonna. Though her career has since continued to flourish and a different Pope dons the holy robes, the singer noted in a 2020 interview that not that much has changed in the world since that controversy. For one, the church still likes to dabble with the playlist, here and there.