In The Number Ones, I’m reviewing every single #1 single in the history of the Billboard Hot 100, starting with the chart’s beginning, in 1958, and working my way up into the present.

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Lulu – “To Sir With Love”

HIT #1: October 21, 1967

STAYED AT #1: 5 weeks

Here’s something funny: 1967, in the popular imagination at least, was the year that the entire baby boom generation was figuring out how to question authority. And yet the biggest single of the year was a love song for an authority figure.

I’ve never seen James Clavell’s movie To Sir, With Love, but it’s a foundational part of that whole “saintly teacher figures out a way to reach tough and wild teenagers” mini-genre. In recent decades, most of those movies have been about white teachers and mostly-black students. To Sir, With Love is about a black teacher, Sidney Poitier, and mostly-white students. The movie was a huge hit, one of the biggest of 1967. (It was #7 on the list, between You Only Live Twice and Thoroughly Modern Millie.) And its theme song, from the 19-year-old Scottish singer Lulu, was a dominant pop smash — the “Gangsta’s Paradise” of its era.

Lulu had never had a real American hit before “To Sir With Love,” but she was a known quantity in the UK. She belonged to the Dusty Springfield line of white British women singing R&B, and her biggest song before “To Sir With Love” was a 1964 cover of the Isley Brothers’ “Shout.” Maybe that’s how she got cast in To Sir, With Love, making her film debut as one of the movie’s rebellious teenagers, and how she ended up singing the song to Poitier at the end of the movie.

On the record, as in the movie, Lulu’s backing band was the post-Wayne Fontana Mindbenders, who’d hit #1 two years earlier with “The Game Of Love.” And the music, while simple, does a nice job combining the beat-driven excitement of British Invasion rock (which must’ve sounded slightly anachronistic in 1967) with the orchestral sweep of a classic movie-theme weeper.

But what really sells the song is Lulu, who brings a wide-eyed candor and sincerity to the song’s gooey sentiments: “If you wanted the sky / I would write across the sky in letters / That would soar a thousand feet high / ‘To sir, with love.'” She’s got a big voice, and she does a few melismatic runs, but she never sounds like she’s trying to be Aretha Franklin. Instead, she sounds sad and wistful, like she really is devoted to this role model who’s about to disappear from her life. When the chorus hits and the drums get loud, it’s like a quickening heartbeat, like she’s screwing up her courage to tell this adult how much he means to her.

Lulu never had another huge American hit, but she kept working. She hosted a TV show that’s mostly remembered for the time when Jimi Hendrix refused to sing with her. She sang the theme for the lesser Roger Moore Bond movie The Man With The Golden Gun. She was married to the Bee Gees’ Maurice Gibb for a few years. And she’s still performing; earlier this year, she played the lead in a West End revival of 42nd Street. Maybe she’s the authority figure now.

GRADE: 8/10

BONUS BEATS: Here’s 10,000 Maniacs and Michael Stipe covering “To Sir With Love” in 1993:

BONUS BONUS BEATS: Here’s Cecily Strong and Sasheer Zamata singing “To Sir With Love” for Barack Obama on the last Saturday Night Live of his presidency:

THE NUMBER TWOS: Sam And Dave’s raw Southern R&B jam “Soul Man,” written by Isaac Hayes and Dave Porter, spent three weeks at #2, stuck behind “To Sir With Love.” It would’ve been a 9. Here it is: