"Last Kiss" was originally a hit for J. Frank Wilson & The Cavaliers in 1964. Their version went to #2 in the US, kept from the top spot by "Baby Love" by The Supremes. On June 26, 1999, Pearl Jam's cover also went to #2, held off by "If You Had My Love" by Jennifer Lopez. The song has a bouncy melody but is very grim. It's about a teenage couple who get in a car crash; the girl dies in the boy's arms. It's based on a true story, something Pearl Jam probably didn't know when they recorded it.
Pearl Jam lead singer Eddie Vedder came across this song when he found the J. Frank Wilson & The Cavaliers record in an antiques store in Seattle before a show. He bought it and stayed up all night listening to it, then he took it to the band and they worked up the arrangement. Pearl Jam played it live a handful of times in 1998, first at a show in Seattle on May 7. They recorded it at a soundcheck and sent it to their fan club members as the holiday single, an annual tradition for the band since 1991. (Pearl Jam's holiday singles aren't usually holiday songs, and when they are, they can be a bit macabre. Their 1992 single was "Who Killed Rudolph?" So sending a song about a tragic car accident wasn't out of character.) The song wasn't released to the public, but after a while, radio stations got copies and started playing it. By the spring of 1999, it was getting a lot of airplay and becoming a hit, even though it was not released as a single or available on an album. On May 29, 1999, it entered the Hot 100 on airplay alone at #84. Pearl Jam loved how the song spread organically without being officially released, but at the behest of their management and record label, they granted permission to issue it as a single to the public with the proviso that proceeds be donated to various international aid groups. The official release came on June 8, 1999, almost six months before they sent it to fan club members. With sales figures to help it along, the song shot from #49 to #2, a giant leap.
The week after "Last Kiss" was issued as a single, it appeared on the album No Boundaries: A Benefit for the Kosovar Refugees, which raised funds for aid groups helping those affected by the Kosovo War.
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