Should've Known Better

Should've Known Better: Richard Marx and the Long Road to Number Three

An Overnight Success With a Very Long Night

When Richard Marx's self-titled debut album arrived in the summer of 1987, it looked to the outside world like one of pop music's cleaner origin stories: a polished young singer-songwriter from Chicago with cheekbones made for MTV and a voice that could sustain a power ballad across four minutes without once breaking a sweat. What the story rarely acknowledged was the decade of dues that preceded that debut: years in Los Angeles writing songs for other artists, working as a backup singer, and absorbing the mechanics of commercial pop from the inside out. Should've Known Better, the third single from that debut, was the song that carried all of that education to its peak.

The Debut Album's Third Act

The album Richard Marx had already produced two successful singles before Should've Known Better was released. The strategy was methodical: let the album build, let the audience develop a relationship with the artist, then send a song that could sustain their attention across the full late-fall and winter radio season. The song debuted on the Billboard Hot 100 on September 26, 1987, entering at number 64. The pace of its ascent was steady rather than explosive: 64, then 51, then 41, through the 20s and teens as autumn deepened.

Marx had written the song himself, and it bore the hallmarks of someone who had spent years studying what worked in commercial pop: the ascending pre-chorus that releases into an open, melodically generous hook; the middle eight that provides emotional contrast without derailing the song's momentum; the key change in the final chorus that lifts the performance to its emotional ceiling. Every structural choice was intentional and every one landed.

Peaking at Number 3

Should've Known Better peaked at number 3 on December 12, 1987, spending 21 weeks on the Billboard Hot 100 in total. That 21-week run was exceptional for a debut act and spoke to the song's specific quality: not just immediate appeal but staying power, the ability to be heard repeatedly without wearing out its welcome on pop radio. The track's success helped the album reach double-platinum status in the United States, an achievement that confirmed Marx as a major commercial force rather than a one-single curiosity.

The Quiet Craft Behind the Polish

What separated Marx from a good number of his late-1980s pop contemporaries was his grasp of song construction as a discipline rather than an accident. He had learned to write in Nashville's back rooms and Hollywood demo sessions, and he brought to his own recordings a craftsman's attention to detail. The production on Should've Known Better was bright and radio-optimized in the way of 1987 pop, with synthesizers and reverbed drums prominent in the mix, but the underlying song was strong enough to survive any production style. That underlying melodic strength was the real achievement, the quality that separated lasting commercial pop from period-specific novelty.

The late 1980s were an interesting moment for adult contemporary pop: synth-based production was everywhere, MTV was reshaping how audiences discovered music, and the market for polished ballads from photogenic male singer-songwriters was larger than it had been in years. Marx understood the landscape and wrote for it without being captured by its superficiality. The result was a catalog of songs that remained on radio long after the synthesizers stopped sounding current.

A Song Worth Returning To

Listening to Should've Known Better now is a reminder that commercial and crafted are not opposites. The song is efficient, emotionally direct, and exactly as long as it needs to be. Marx had spent years learning how to do this well, and it shows in every measure.

Put it on the next time someone tells you pop songwriting is not a real skill.

"Should've Known Better" — Richard Marx's singular moment on the 1980s charts.