Should've Known Better (Richard Marx song) "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 . The song peaked at number three 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 . In the lyrics, the speaker is still in love with an ex-lover and tortured by it, to the point of regretting falling in love with her.The music video for the selection was directed by Dominic Sena .Personnel Richard Marx: lead vocals, backing vocals Tom Keane: keyboards Michael Landau: guitar John Pierce: bass guitar Prairie Prince: drums Paulinho da Costa: percussion Fee Waybill: backing vocalsChart performance Released in September 1987 as the second single from his debut solo album , "Should've Known Better" entered the U.S. Billboard Hot 100 on September 26 , 1987 at number 64 , the highest debut of the week. The single also peaked at number 20 on the U.S. Adult Contemporary chart. The song also reached #4 on the Radio & Records CHR/Pop Airplay chart on November 20 , 1987 for two weeks and remained on the chart for 13 weeks. Elsewhere, the single reached number 50 in the United Kingdom .Charts Year-end charts
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