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Shaggy’s Reggae Spin on the Sinatra Songbook Lands a 2023 Grammy Nod

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Shaggy’s Com Fly Wid Mi, which consists of 11 songs made famous by Frank Sinatra, is competing for a Grammy in the best reggae album category. The album’s title, of course, is a reggafied twist on Sinatra’s jet-age classic “Come Fly With Me.”

Two previous Sinatra tribute albums won Grammys for best traditional pop vocal album – Tony Bennett’s Perfectly Frank (1992) and Willie Nelson’s My Way (2018). Seven others were nominated in that category — Barry Manilow’s Manilow Sings Sinatra (1999), Keely Smith’s  Keely Sings Sinatra (2001), Michael Feinstein’s The Sinatra Project (2008), Bob Dylan’s Shadows in the Night (2015), Fallen Angels (2016) and Triplicate (2017) and Nelson’s That’s Life (2021).

The Recording Academy says Shaggy’s album was submitted in the best reggae album category and was accepted by the reggae screening committee. It was never considered in the traditional pop category. 

Copy on the front cover of the album describes the project this way: “The Sinatra songbook inna reggae style. Sung by Shaggy. Produced by Sting.” Sting also sings on two of the tracks, “You Make Me Feel So Young” and “Witchcraft.” A collaborative album by Sting and Shaggy, 44/876, won a Grammy for best reggae album four years ago.

The other tracks on Com Fly Wid Mi are “That’s Life,” “Come Fly with Me,” “That Old Black Magic,” “Fly Me to the Moon,” “Luck Be a Lady,” “I’ve Got You Under My Skin” [shown here as “Under My Skin”], “Saturday Night Is the Loneliest Night of the Week” [shown here as “Saturday Night”), “Angel Eyes” and “Witchcraft” [a guitar and vocal “bonus track”].

This is Shaggy’s eighth nomination for best reggae album. He has won twice in the category for Boombastic (1995) and the aforementioned 44/876. Shaggy’s only nomination outside of this category was for “It Wasn’t Me,” a collab with Ricardo “RikRok” Ducent, which was nominated for best pop collaboration with vocals. The song topped the Billboard Hot 100 for two weeks in February 2001.

Sinatra’s “Come Fly With Me” was one of his most iconic hits. His album of the same name topped the Billboard 200 for five consecutive weeks in February and March 1958 and received Grammy nominations for album of the year and best vocal performance, male in the first year of the Grammys. The album was inducted into the Grammy Hall of Fame in 2004.

Sinatra, widely regarded as one of the finest vocalists of the 20th Century, won nine Grammy Awards, from 1958 (best album cover for his design work on Frank Sinatra Sings for Only the Lonely) to 1995 (best traditional pop vocal album for Duets II).

Sinatra was the first artist to win album of the year twice, and also the first artist to win it three times. In all the years since, just three other artists have won album of the year three times as a lead artist – Stevie Wonder, Paul Simon (counting a Simon & Garfunkel album) and Taylor Swift. Adele would join their ranks if she wins at the 65th annual Grammy Awards on Feb. 5.

Sinatra received a lifetime achievement award from the Recording Academy in 1966, a trustees award in 1979 and a Grammy legend award in 1994. Bono presented the latter award after delivering an exquisitely written speech. A clearly moved Sinatra, who was 78 at that point, started to ramble in his acceptance remarks. Unfortunately, the Grammy production team cut him off mid-speech and cut to a commercial. The explanation was they didn’t want the great star to embarrass himself on live TV. That may well be, but it could have been handled with more foresight and grace. This was Sinatra’s final appearance on the Grammy telecast. He died in 1998 at age 82.

This year’s other nominees for best reggae album are Kabaka Pyramid’s The Kalling, Koffee’s Gifted, Sean Paul’s Scorcha and Protoje’s Third Time’s the Charm.

The Grammy rules for best traditional pop vocal album say this about what the category is intended to honor: “This category is for performances of a type and style of song that cannot properly be intermingled with present forms of pop music. This includes older forms of traditional pop such as the Great American Songbook, created by the Broadway, Hollywood and Tin Pan Alley songwriters of the period between the 1920s and the end of World War II, as well as cabaret/musical theater-style songs and previous forms of contemporary pop. This would also include contemporary pop songs performed in traditional pop style — the term ‘traditional’ being a reference, equally, to the style of the composition, vocal styling and the instrumental arrangement, without regard to the age of the material.”

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