“How Will I Know” by Whitney Houston (1985)

“How Will I Know” was the song that made Whitney Houston America’s sweetheart. And as calculated as Clive Davis’s plan to make her a superstar were (release a couple of singles that solidified a base of R&B fans before making an all-out pop push), it worked. And it worked with a great song, even if it took me some years to warm up to it (and Whitney in general).

Where “You Give Good Love” and “Saving All My Love For You” were sultry, “How Will I Know” was effervescent. Girlish, even. It makes sense that the song was offered to a teenage, pre-Control Janet Jackson before it ended up in Clive’s hands to be voiced by Whitney. Even though she was barely 21 herself, that voice gave the song a dash of gravity that Janet wouldn’t have been able to muster up at that point.

Add in a colorful video featuring a glammed-up Whitney in a blond wig, and the end result was a Number One pop record (the second of seven in a row for Whitney) and MTV saturation. In the 35 years since, “How Will I Know” has also become a karaoke standard and a benchmark for vocal prowess, as Whitney’s a capella track attests to.

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