Nancy Sinatra Let Jessica Simpson Cover ‘These Boots Are Made for Walkin” Under 1 Condition

Frank Sinatra’s daughter, Nancy Sinatra, is perhaps most known for her classic rock song “These Boots Are Made for Walkin’.” During the 2000s, Jessica Simpson released an R&B-tinged cover of “These Boots Are Made for Walkin’.” Sinatra allowed Simpson to release the cover under one condition.

Frank Sinatra’s daughter had to convince a country singer to give her ‘These Boots Are Made for Walkin”

Lee Hazlewood was a country singer and songwriter. He wrote and produced “These Boots Are Made for Walkin’.” According to a 2021 Rolling Stone article, Hazlewood initially wanted to record the song himself. 

Nancy Sinatra revealed how she convinced Hazlewood that she should sing the song. “I just told him the truth: that I didn’t think it was good for a man to sing it, that it sounded kind of ugly, and that a girl should sing it and it would be better,” she recalled. “And he realized I was right.”

What happened when Jessica Simpson asked Nancy Sinatra for permission to cover the song

During a 2009 interview with PopMatters, Sinatra was asked what she thinks about other artists drawing influence from her and covering her songs. “I love it and take it as a compliment,” she said. “I get a thrill seeing my music and my image live on.”

Sinatra revealed she asked Simpson to do something when she covered “These Boots Are Made for Walkin’.”

“When Jessica Simpson recorded her version of ‘These Boots Are Made For Walkin’,’ she called me and asked for permission,” Sinatra said. “I told her yes, only if she contacted the original bass player Chuck Berghofer and paid him royalties for the bass line.”

Sinatra also discussed the original song’s relationship to Hazlewood. “Lee dictated the bass line to Chuck, but the way Chuck played it was psychotic!” she opined. “I called Chuck to make sure, and Jessica was honorable and kept her word. He got paid.”

How Nancy Sinatra’s ‘These Boots Are Made for Walkin” and Jessica Simpson’s cover performed on the charts

Sinatra’s version of “These Boots Are Made for Walkin'” was a huge hit. According to The Billboard Book of Number 1 Hits, the song became her first No. 1 on the Billboard Hot 100. And the song topped the chart for one week. It was her most successful solo song.

Simpson’s “These Boots Are Made for Walkin'” was a more modest hit. The track peaked at No. 14 on the Billboard Hot 100, staying on the chart for 11 weeks. And it appeared on some editions of Simpson’s album A Public Affair. That album hit No. 5 on the Billboard 200, remaining on the chart for nine weeks.

“These Boots Are Made for Walkin'” is a classic song and became a hit in the hands of two different singers.