"Should've Known Better" is a hit song written, composed, and performed by American rock singer Richard Marx. It was released in September 1987 as the second single from his Triple Platinum-selling self-titled debut album. It was written by Marx and produced by Humberto Gatica.

The song peaked at #3 on the US Billboard Hot 100 as well as #7 on the Billboard Mainstream Rock Tracks chart in 1987, and #4 on the Radio & Records CHR/Pop Airplay chart. Marx became the first solo artist in recording history to reach the top three of the Billboard Hot 100 with four singles from a debut album.

"Should've Known Better" features Michael Landau on guitars, and The Tubes members, Fee Waybill on backing vocals and Prairie Prince on drums.

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