The classic Frank Sinatra song that held the number-one spot for the longest

When you dive into it, the career of Frank Sinatra is utterly fascinating.

He’s one of those people who goes well beyond a household name to being deemed a legend, almost a myth, as his fame is so vast and so lofty, it’s hard to even get a clear picture of the man under it. But with so many accolades to his name, that’s to be expected.

Altogether, spanning his entire six-decade career, Sinatra sold an insane amount of records. The number is estimated to be over 150million, spreading across 59 studio albums, 34 compilations and a grand total of around 169 compilations to his name. That’s a lot of releases, and as his estate keeps dusting off new demos and live tapes, the number keeps on growing.

But the interesting part of Sinatra isn’t his statistics, but the intrigue is in the wild eras of his life, starting with his early rumoured connection to the mafia and his ‘Rat Pack’ days, to the times spent threatening the 1960s crowd. From being the ultimate heartthrob of music, to verbally scrapping with The Beatles, the timeline of his work is full of twists, turns and odd little stories and conspiracies, only adding to the expansive, seemingly endless nature of his legacy.

Amongst all of that, there are countless hits that span seemingly every era, starting with ‘Polka Dots and Moonbeams’ in 1940 before going from strength to strength with ‘Young at Heart’, ‘Come Fly With Me’, ‘That’s Life’ and ‘My Way’ throughout the late 1950s and ‘60s. Everybody seems to know those songs as Sinatra’s renditions became standards, packing his live sets out with his countless crowdpleasers that kept his gigs sold out until the day he died. But in an actual charting way, he had very few successes.

‘Ol’ Blue Eyes’ was never really a chart smash, such that, in his entire career, he only bagged the top spot twice, despite recording some of the most iconic tracks of the entire 1900s.

How many number ones did Frank Sinatra have?

When it comes to the Billboard Top 100, the two times he took the top spot were once in 1966 with ‘Strangers In The Night’, and then again in 1967 with ‘Somethin’ Stupid’. Strangely, both came after what might have been considered his true golden period.

He bagged the two trophies during his attempted comeback period after he’d reinvented his old 1950s persona into a more weathered and classic lounge lizard crooner type, leaning into the archetype he’d been cast in rather than trying to battle against it.  ‘Strangers In The Night’ hit number one, stayed there for one week only and then was replaced by The Beatles’ ‘Paperback Writer’, but ‘Somethin’ Stupid’ stuck around.

How long was ‘Somethin’ Stupid’ number one?

As Frank Sinatra’s longest-running number one hit, his duet with his daughter Nancy Sinatra held onto the number-one Billboard chart spot for four weeks, and on the easy listening charts, it kept the trophy for an impressive nine-week run. Overall, the single has sold around two million copies, but the luck of the song rubbed off on another set of artists as the duet between Robbie Williams and Nicole Kidman also earned a gold certification as people seemed to like the song more when it wasn’t somewhat creepily sung by a father and daughter duo.

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