Dolly Parton – 1997 Cadillac, $33.9K

Dolly Parton stands as an iconic figure in the realm of country music, with accolades that have set her apart as one of the most celebrated female artists in the genre. She boasts the distinction of being the first woman to land 25 songs at the pinnacle of the Billboard country charts, alongside a plethora of prestigious awards.

Beyond her musical achievements, Parton’s love for motorcycles reveals another facet of her dynamic personality. Although she has the means to acquire any vehicle, her cherished possession remains a silver 1997 Cadillac, a car that held a starting price of $36,995 in the late ’90s—remarkably lower than today’s prices.