June 14, 1997: Puff Daddy debuted at the top of Billboard's Hot 100 chart with "I’ll Be Missing You."
Rap’s underground/mainstream schism dates to the moment Puff Daddy’s performative act of mourning took over the Hot 100 and became, quite possibly, the biggest rap hit in history to that point.
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Underground rap had certainly existed before “I’ll Be Missing You,” but the late-’90s underground boom pretty much happened as a stern and direct rebuke to what Puff Daddy was doing.
Read more: Stereogum
June 14, 1969: After a dry spell, Elvis Presley reached Number 3 on the US music chart with "In The Ghetto."
The Mac Davis penned “In The Ghetto” closed out the excellent album From Elvis In Memphis and was part of a legendary Memphis session that included recordings of “Suspicious Minds,” “Kentucky Rain” and “Don’t Cry Daddy,” songs which laid the groundwork for The King’s comeback from the musical doldrums of his movie years.
Read more: American Songwriter
June 14, 1975: Harold Melvin & the Blue Notes' American Top 20 hit "Bad Luck" peaks at Number 15.
June 14, 1980: Joe Walsh's "All Night Long" became one of four Top 40 charting songs in his solo career.
"All Night Long" appears in the soundtrack to the film Urban Cowboy. Unlike the other tracks from the film, it doesn't have much to do with country music—despite its reference to chewing tobacco: "Keep a-grinning 'til the weekend comes / Just a pinch between your cheek and gum."
Read more: Wikipedia
June 14, 1986: "I Can't Wait" by Nu Shooz topped out at Number 3 in the US.
Jim Blashfield created the video for Nu Shooz using animation techniques he had applied in short films. "I Can't Wait" places Valerie Day is a surreal, whimsical universe. His other videos include Michael Jackson's "Leave Me Alone," Tears For Fears' "Sowing the Seeds of Love," and Talking Heads' "And She Was."
Read more: Songfacts
I’ll Be Missing You
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