I remember that in the late '90s there was a resurgence of interest in the old "Rat Pack" and its members and their works. Thus did we see, for example, a homage of sorts to the group in Doug Liman's Swingers, the Steven Soderbergh remake of Ocean's Eleven that launched a whole cinematic franchise, and such oddities as Larry Bishop's Mad Dog Time, as Ray Liotta played the actual Frank Sinatra in HBO's film The Rat Pack. (Meanwhile remembrances of the group cropped up in a good many smaller ways--as with Brent Spiner's rendition of Dean Martin's "Sway," as seen in the film Out to Sea--itself a piece of nostalgia in its reunion of Jack Lemmon and Walter Matthau.)
The boom in Rat Pack nostalgia waned, but something of it seemed to come back a decade or so later, helped perhaps by the obsession of a culturally influential stratum with the aesthetic of the '50s as Mad Men became a hit.
However, a decade after there was no repeat of that. The only really significant usage of the Rat Pack's work in pop culture in the late '10s was in Todd Phillips' Joker--a film which, significantly, was itself a throwback (to the work of Martin Scorsese in the '70s and early '80s), and in which the particular theme of "Send in the Clowns" was highly relevant (and probably the reason the film also used Sinatra's rendition of "That's Life" in the end credits).
Some might see cultural politics in that, identifying nostalgia for the Rat Pack with a kind of machismo of which the mainstream has been less and less approving, with the #MeToo era a low point for such tolerance. However, one can also see it as a matter of how in popular memory even as grand a legacy as that of Frank Sinatra and his cohorts fades--perhaps the more quickly with pop culture getting ever more fragmented, and popular memory getting shorter all the time.
Solomon Kane - Rattle of Bones
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