1965 “Help!” The Beatles
1966 “Monday, Monday” The Mamas & the Papas
1964 “My Guy” Mary Wells
1962 “The Loco-Motion” Little Eva
1968 “This Guy’s in Love With You” Herb Alpert
1967 “Somethin’ Stupid” Frank & Nancy Sinatra
1960 “It’s Now or Never” Elvis Presley
1969 “Hot Fun in the Summertime” Sly and the Family Stone
1961 “Pony Time” Chubby Checker
1963 “Fingertips” Little Stevie Wonder
IMO, there’s a big gap between the first two on my list and the rest of them.
1969 “Hot Fun in the Summertime” Sly and the Family Stone
BTW, my list was 1-10 and ignore the second mention of Hot Fun In The Summertime underneath the comment.