2019: Lizzo's "Truth Hurts" beat Billie Eilish's "Bad Guy" for best pop solo performance, but their fortunes were reversed in record of the year. Likely reason: Voters didn't want Lizzo to be shut out in the high-profile categories. They also may have thought that Lizzo's playful vocal performance was especially important to the success of "Truth Hurts."
1975: Eagles' "Lyin' Eyes" beat Captain & Tennille's "Love Will Keep Us Together" to win best pop vocal performance by a duo, group or chorus, but it was the other way around for record of the year. Likely reason: The voters were saluting Eagles' impeccable vocal harmonies in the performance award. The record of the year prize saluted C&T's smash, which was far and away the most popular single of 1975. The spunky arrangement, which seemed to find the precise midpoint between the energy of Elton John and the romanticism of Carpenters, sounded fresh at the time. But Eagles weren't bridesmaids in the top category for long: "Hotel California," the title track of their very next studio album, won the 1977 award for record of the year.
1970: Carpenters' "(They Long to Be) Close to You" beat Simon & Garfunkel's "Bridge Over Troubled Water" for best contemporary vocal performance by a duo, group or chorus, but S&G prevailed for record of the year. Likely reason: The voters sensed that the majestic "Bridge," the year's longest-running No. 1 hit on the Billboard Hot 100, would sweep the top awards, but wanted to find a way to salute and welcome Carpenters, fronted by Karen Carpenter, a one-of-a-kind vocal talent. "Close to You" was their breakthrough single.
1964: Barbra Streisand's "People" beat (Stan Getz and) Astrud Gilberto's "The Girl From Ipanema" for best vocal performance, female, but there was a reversal of fortune for record of the year. Likely reason: Streisand's powerful vocal was the main draw on "People." "The Girl From Ipanema" had other things going for it, including the record's sensuous vibe and the international bossa-nova wave its success triggered.
1959: Frank Sinatra's Come Dance With Me (the album of the year winner) won best vocal performance, male, beating Bobby Darin's "Mack the Knife." (Back in the day, albums and singles sometimes competed in the same performance categories.) "Mack the Knife" won record of the year, beating Sinatra's "High Hopes" (which was not drawn from Come Dance With Me). Likely reason: Sinatra had lost in the male vocal category the year before to Perry Como. Voters didn't want to let the great Sinatra down two years running.
1958: In the first year of the Grammys, Como's "Catch a Falling Star" beat Domenico Modugno's "Nel Blu Dipinto Di Blu (Volare)" for best vocal performance male, but they flip-flopped for record of the year. Likely reason: The smooth Mr. C was both a top TV and recording star, with hits under his own name going back to 1943 (and even further back singing with Ted Weems and his Orchestra). Modugno was an untested newcomer. Indeed, as it turned out, he never landed another top 40 hit on the Hot 100.