If Tony Bennett and Lady Gaga’s Love for Sale wins the Grammy for album of the year on Sunday (April 3), the two stars need to really thank the Recording Academy, which decided the album could compete this year.

The album’s eligibility was in question. The collection of Cole Porter songs was released in some configurations — including cassettes — on Sept. 30, 2021, the last day of eligibility for the 64th annual Grammy Awards. The album was released in all other configurations on Oct. 1. The Academy decided to treat Sept. 30 as its day of release.

The last album of the year winner that was released on the last day of the eligibility year was Bob Dylan’s Time Out of Mind, which won the 1997 award. (Apparently, legends like to cut it close!)

Eight times in Grammy history, an album that was released in the final month of the eligibility year wound up winning album of the year. Here’s a full list:

1958: Henry Mancini’s The Music From Peter Gunn

Release date: By all accounts, this album was released in January 1959. The last date of the Grammy eligibility year was Dec. 31, 1958. (This was the first and only time the Grammys used a calendar year as their eligibility year.) A 1995 RCA box set of Mancini’s most memorable works, The Days of Wine and Roses, lists the album’s release date as “1/59.” So what’s the story? The Academy may have bent the rules to let the album compete, not even knowing if the awards would make it to a second year. Or it may have just been a gaffe. This was decades before the Internet made double-checking facts easy.

About the album: This was the first and only TV soundtrack to win album of the year. The album beat two classic Frank Sinatra releases, Come Fly With Me and Frank Sinatra Sings for Only the Lonely. Sinatra was not pleased. Fortunately, he was nominated again the following year with Come Dance With Me!. This time he won. Phew!

1962: Vaughn Meader’s The First Family

Release date: The album was released in November 1962; the eligibility year ended on Nov. 30.

About the album: This was the second comedy album in three years to win album of the year; the first that dealt in political humor. The album gently tweaked (by current comedy standards) John F. Kennedy and his family. JFK was assassinated in Dallas a little more than six months after this was named album of the year.

1975: Paul Simon’s Still Crazy After All These Years

Release date: Simon’s album was released on Oct. 6, 1975, nine days before the end of the eligibility year.

About the album: This was Simon’s first solo album to take the top award. Simon & Garfunkel’s Bridge Over Troubled Water had won the award five years earlier.

1976: Stevie Wonder’s Songs in the Key of Life

Release date:  This classic double album was released on Sept. 28, 1976, two days before the end of the eligibility year.

About the album: This was Wonder’s third consecutive studio album to win the award, following Innervisions and Fulfillingness’ First Finale. No one else has ever done that, though Adele could equal the feat if she wins at the 65th annual Grammy Awards in January 2023. (Just keep it in mind…)

1997: Bob Dylan’s Time Out of Mind

Release date: The album was released on Sept. 30, 1997, the last day of the eligibility year.

About the album: This was the first (and is still the only) Dylan album to win album of the year. (Better late than never!) Dylan had won an album of the year trophy as one of many artists on The Concert for Bangla Desh, the 1972 winner, but George Harrison was the lead artist on that album. Time Out of Mind won a second award as best contemporary folk album.

2003: OutKast’s Speakerboxxx/The Love Below

Release date: The double album was released on Sept. 23, 2003, one week before the end of the eligibility year.

About the album: This was the second hip-hop album to win album of the year, following Lauryn Hill’s The Miseducation of Lauryn Hill. It’s also the most recent one to win. Speakerboxxx won a second award as best rap album.

2007: Herbie Hancock’s River: The Joni Letters

Release date: The album was released on Sept. 25, 2007, five days before the end of the eligibility year.

About the album: This was the second jazz album to win album of the year, following Stan Getz and João Gilberto’s Getz/Gilberto. That 1964 album included the global bossa nova smash “The Girl from Ipanema.” River: The Joni Letters won a second award as best contemporary jazz album.

2012: Mumford & Sons’ Babel

Release date: The album was released on Sept. 21, 2012, nine days before the end of the eligibility year.

About the album: Babel won album of the year, even though it lost in its “genre album” category, best Americana album, to Bonnie Raitt’s Slipstream. Babel was the second album in three years to win the top award without winning its genre album award. Arcade Fire’s The Suburbs, the 2010 album of the year winner, lost best alternative music album to The Black Keys’ Brothers. I guess if you’re going to win one and lose one, you’d want to win the big one.

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