Past Grammy-Winning Albums You Can Stream on Hoopla

Countdown to the Grammy Awards 

The 68^th Annual Grammy Awards will take place on Sunday, February 1 at 8 p.m. ET/5 p.m. PT. Who are you rooting for to win Album of the Year? We’re having trouble deciding, but in the meantime, we’re giving a listen to past winners of the Album of the Year Grammy.  

Listen along with Hoopla’s collection of past Grammy Album of the Year winners. They’re all terrific albums (obviously—they all won a Grammy!), and here are a few highlights of Grammy-winning albums on Hoopla. 

Grammy Award-Winning Albums on Hoopla 

Is your favorite album on this list? Maybe, and maybe your next favorite album is on this list, waiting for you to hear it! (Note: Grammys are handed out in the calendar year that follows the year in which the album was released. Each year listed is the year the album won a Grammy.) 

Frank Sinatra has won an Album of the Year Grammy for three of his albums; Come Dance with Me! (1960), and back-to-back September of My Years (1966) and A Man and His Music (1967). It’s an impressive number, but not the most Grammys an artist has won for Album of the Year. Read on to find out who holds that record. 

Stevie Wonder has also won three Grammys for Album of the Year, including Songs in the Key of Life (1977), which is 50 years old in 2026 (it was released in 1976). Fulfillingness’ First Finale (1975) earned Wonder back-to-back Album of the Year Grammys and was the second he would win in four years.  

Fleetwood Mac’s Rumours (1978) is one of the the top-circulating albums on Hoopla. That’s no surprise when you consider that it features some of the greatest pop songs of all time, including “Dreams,” “Go Your Own Way,” and “Don’t Stop.”

Saturday Night Fever (1979), the movie soundtrack, is #5 on Billboard’s ranked list of Album of the Year Grammy winners. If that surprises you, you need to give it a(nother) listen—it includes “If I Can’t Have You” by Yvonne Elliman, “More Than a Woman” by Tavares, and four groovy hits by the Bee Gees (including their version of “More Than a Woman”). 

Nick of Time (1990) was Bonnie Raitt’s 10th studio album, but it was the powerhouse singer-songwriter’s breakthrough into mainstream stardom. As of 2025, Raitt has won 13 Grammy Awards from 31 nominations. 

Who is the youngest artist ever to win an Album of the Year Grammy?

That would be Billie Eilish, who was just 18 when she won for When We All Fall Asleep, Where Do We Go? (2020). She was also the first female artist (and second person ever) to win each of the “big four” Grammy Awards in one night, winning not only best album for When We Fall Asleep… but also Record of the Year, Song of the Year, and Best New Artist. What a night! (The first male artist to do so was Christopher Cross in 1981.) 

If you’re wondering who holds the record for most Album of the Year Grammys, the answer is none other than Taylor Swift, with four: Fearless (2010), 1989 (2016), Folklore (2021), and Midnights (2024). Midnights includes “Anti-Hero,” which spent nine weeks at #1 on Billboard’s Hot 100 list, the longest of any of her songs until “The Fate of Ophelia” surpassed it this year.   

Stream Grammy Winners on Hoopla 

All you need is a library card and Hoopla to stream these Grammy winners and more. They’re all part of Hoopla’s collection of past Grammy Album of the Year winners. And they should keep you busy until the 2026 Album of the Year is crowned at the Grammys on February 1. Happy listening! 

*Title availability may vary.