Every year, music enthusiasts eagerly anticipate awards shows, only to engage in a popular pastime: critiquing the selections. Social media platforms erupt with critiques during events like the Oscars, Golden Globes, and Country Music Awards. The Grammys, often hailed as the pinnacle of musical achievements, are no exception. As the "biggest night in music" approaches, it's intriguing to revisit some of the most questionable Album of the Year nominees from the past. Despite the category featuring some of the greatest albums ever made, there have been several puzzling choices that left many scratching their heads.

One recurring theme is duplication. In 1960, just the second year of the Grammys, Henry Mancini’s Peter Gunn soundtrack received a second nomination for more tracks from the same film, even though it had already won the previous year. Similarly, in the early '70s, two versions of the same musical, Jesus Christ Superstar, were nominated back-to-back. Neither version won, but the repetition raised eyebrows.

Sometimes, the Grammy voters seemed out of touch with contemporary trends. For instance, Barbara Streisand’s The Broadway Album was nominated in 1987, despite her peak being over a decade earlier. That same year, iconic albums like License to Ill by Beastie Boys were overlooked. Similarly, in 1995, the live recording of The Three Tenors in Concert took a slot that could have gone to groundbreaking works by Green Day, Jeff Buckley, or Nine Inch Nails. These nominations felt particularly offbeat given the vibrant alternative and grunge scenes of the time.

Occasionally, the Grammys belatedly recognized artists who deserved acknowledgment earlier. Bob Dylan’s Time Out of Mind (1998) and Steely Dan’s Two Against Nature (2001) finally earned accolades long after their prime years. While these albums were indeed exceptional, they highlighted how the Grammys sometimes missed out on recognizing artists in their heyday. Pearl Jam’s Ten, for example, never received a nod when it first came out, reflecting a broader trend of the Grammys lagging behind cultural shifts.

Then there were the truly undeserving winners. Boz Scaggs’ Silk Degrees (1977), Kim Carnes’ Mistaken Identity (1982), MC Hammer’s Please Hammer Don’t Hurt ‘Em (1991), and the Backstreet Boys’ Millennium (2000) all secured spots on the prestigious list. Each of these albums, while commercially successful, lacked the artistic depth and innovation expected of an Album of the Year nominee. In particular, the inclusion of MC Hammer’s album in a year that also saw releases from N.W.A. and Metallica seemed especially misplaced.

Nominees whose names alone raised questions included Sting’s …Nothing Like the Sun (1989), Gwen Stefani’s Love. Angel. Music. Baby. (2006), and Amy Grant’s Heart in Motion (1992). These selections suggested that the Grammy voters might not have fully grasped the pulse of popular music. Amy Grant’s nomination, for instance, overshadowed pivotal albums like Nirvana’s Nevermind and Red Hot Chili Peppers’ Blood Sugar Sex Magik.

Lastly, some nominations bordered on the bizarre. Allan Sherman’s comedy album My Son the Folk Singer (1963), Soeur Sourire’s The Singing Nun (1964), and The 5th Dimension’s The Age of Aquarius (1970) all found their way onto the list. These quirky picks underscored how far the Grammy committee would sometimes stray from mainstream tastes. Notably, “We Are the World” (1986) by USA for Africa dominated airwaves despite its somewhat awkward composition, further highlighting the disconnect between public sentiment and Grammy recognition.

In examining these controversial nominations, it becomes clear that while the Grammys aim to celebrate the best in music, they occasionally miss the mark. Whether through repetition, outdated preferences, or simply poor judgment, these selections remind us that even the most prestigious awards can stumble. Yet, each misstep offers valuable insight into the evolving landscape of music and the challenges of defining what truly deserves recognition.