Will Cyndi Lauper win a second Grammy 29 years later?

After winning Best Musical at the Tony Awards this summer, Cyndi Lauper‘s “Kinky Boots” now competes at the Grammys for Best Musical Theater Album. Can it triumph again?

Lauper made her Grammy Awards debut in 1984, winning Best New Artist against Corey Hart, Sheila E., Frankie Goes to Hollywood, and The Judds.  She is one of only of eight artists to be nominated for the top four categories in the General Field and win Best New Artist. The others are Bobbi Gentry (1967), Christopher Cross (1980), Tracy Chapman (1988), Mariah Carey (1990), Paula Cole (1997), Amy Winehouse (2007), and Fun. (2012).

Lauper has received 14 nominations in various genres fields ranging from Pop to Rock to Dance to Blues to Arranging. All but one of those bids resulted in losses, but this year she may add Musical Show to her diverse list of Grammy field nods.

At the Grammys, unlike the Tonys, the Best Musical Theater Album award includes both new Musicals and Musical Revivals in this one category. In the past 20 years of this category’s history, the Tony winner was in synch with the Grammy winner 12 times. Four wins were for revivals.

Only two times has the Grammy winner not been nominated for either Best Musical or Best Revival of a Musical at the Tonys (“Riverdance,” 1996; “Aida,” 2000).

In 2002, the “Hairspray” soundtrack album competed at the Grammys one year before its victory at the Tonys.  This discrepancy spoiled the Grammy chances for 2002 Tony winners “Thoroughly Modern Millie” (new musical) and “Into The Woods” (revival).

Six times a Tony nominee got revenge against the Tony winner by winning the Grammy: “The Who’s Tommy” beat “Kiss of the Spiderwoman,” 1993; “Smokey Joe’s Cafe” beat “Sunset Boulevard,” 1995; “Gypsy” beat “Nine,” 2003; “Wicked” beat “Avenue Q,” 2004; “West Side Story” beat “Hair,” 2009; and “American Idiot” beat “Memphis,” 2010.

Kinky Boots” could be battling other newcomers “A Christmas Story,” “Bring It On,” and “Matilda” and/or revivals “Pippin” (Tony winner), “Annie,” “The Mystery of Edwin Drood,” and “Rodgers and Hammerstein’s Cinderella.”

This year, Lauper won Best Original Score at the Tony Awards, bringing herself one award closer to accomplishing an EGOT.  In addition to her 1984 Grammy, she won an Emmy for Best Comedy Guest Actress for “Mad About You” in 1995.  Now with her Tony award win, she is in need of an Oscar to complete the awards quartet.

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