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Two versions of the same song were Billboard Hot 100 hits in 1999

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Yep, NSYNC's "(God Must Have Spent) A Little More Time on You" peaked at number eight in February and six months later, Alabama's cover with NSYNC as featured artists peaked at number 29.

All milestone US number one singles

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Includes those from Your Hit Parade (1935-40), Billboard pre-Hot 100 (1940-58) and Billboard Hot 100 (1958-present). 100th (seventh Billboard pre-Hot 100) - "Maria Elena" by Jimmy Dorsey (1941) 100th (pre-Hot 100, 193th overall) - "Chattanoogie Shoe Shine Boy" by Red Foley (1950) 200th (107th Billboard pre-Hot 100) - "The Thing" by Phil Harris (1950) 300th (20th Billboard Hot 100) - "Mack the Knife" by Bobby Darrin (1958) 100th (Hot 100, 380th overall) - "Deep Purple" by Nino Tempo and April Stevens (1963) 400th (120th Billboard Hot 100) - "Baby Love" by The Supremes (1964) 200th (Hot 100, 480th overall) - "Honey" by Bobby Goldsboro (1968) 500th (220th Billboard Hot 100) - "I Can't Get Next to You" (1969) 300th (Hot 100, 580th overall) - "The Morning After" by Maureen McGovern (1973) 600th (320th Billboard Hot 100) - "Dark Lady" by Cher (1974) 400th (Hot 100, 680th overall) - "K...

While the Billboard Hot 100 began in 1958

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In actuality, the American singles chart from Billboard magazine began in 1940, though the earliest example was in fact the chart for the NBC radio show Your Hit Parade , which began in 1935 before it ended a week before Billboard began their singles chart.