Simon & Garfunkel (1970)

Simon & Garfunkel's 1970 breakup remains the most bitter in folk-rock history, driven by Paul Simon's jealousy over Art Garfunkel's acting career and Garfunkel's resentment of Simon's creative control. Despite producing the era's best-selling album, Bridge Over Troubled Water, with 6x Platinum US sales, their live chemistry evaporated. The rift was so deep that their 1981 Central Park reunion drew 500,000 fans but sparked renewed arguments, making their split more dysfunctional than #10 Fleetwood Mac's 1987 firing of Lindsey Buckingham. While Fleetwood Mac's drama produced another three decades of music, Simon & Garfunkel's tension halted collaborations, proving that ego clashes can outweigh even platinum success.