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Depends on your criteria. When you consider the top 40 pop charts, USA only (today you would look at the top 10 positions on the Billboard Hot 100) the list narrows considerably. Here are the definites.... Louis Armstrong
Bing Crosby
Perry Como
Michael Jackson
Cher With an Asterisk:
Barbra Streisand, 1960s, 70s, and 1980s, and a top 10 duet in 1996 with Bryan Adams, I Finally Found Someone.
The Beatles, as long as you count individual members' hits during the 1980s. The group returned to the top ten as a group with 1995's Free As a Bird.
The Mills Brothers, had success in 1928-1929 but top ten cannot be historically confirmed. They went on to score number one hits in the 1930s, 1940s, and 1950s, and flirted with the top 20 as late as 1968. If we broaden the list to include other music charts, including Adult Contemporary, Country, Top Airplay, etc., the list grows considerably; here are a few notables: Elvis Presley
The Bee Gees
Neil Diamond
Eddy Arnold
Rod Stewart
Elton John
Frank Sinatra
and a few others.
If you venture into the UK Charts, the list grows even longer. Cliff Richard and Elvis Presley have both had top ten hits on the British charts in SIX decades. The above answer is a synopsis of an article that appears here: http://www.popularsong.org/tidbits2.html
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