Sean Penn Directed 1 of Shania Twain’s First Music Videos

In the early days of her career, Shania Twain was a little-known country singer who was new to Nashville and was trying to find her niche in the market. At a time when she received little support from her record label, the Canadian singer got a boost from an unlikely source: Academy Award-winning actor Sean Penn.

Shania Twain’s debut wasn’t big

Shania Twain released her self-titled debut album in 1993. She admitted in her 2022 Netflix documentary Not Just a Girl and 2011 memoir From This Moment On that she had very little creative input in the album, as her record label gave her songs that they felt would check certain country music boxes and she only co-wrote one song on the album.

Twain’s debut single “What Made You Say That” caused controversy upon its release because she dared to bare her midriff in the video. The song peaked at No. 55 on Billboard’s Hot Country Songs chart, leading the label to believe that there was little gas left in her debut record.

Sean Penn wanted to work with Shania Twain to direct a music video

In her memoir From This Moment On, Twain reflected on a career-changing moment after the release of “What Made You Say That.”

“I learned that actor Sean Penn was interested in directing my next music video,” she remembered. “I still don’t know how he’d even heard of me. Perhaps he watched CMT at the time? I was glad he did, in any case. Frankly, I’m not sure that Mercury [Records] had planned on a follow-up to ‘What Made You Say That,’ but to have someone of Sean’s caliber interested in working with me might have made the label take me more seriously and agree to finance the production. The timing was great, and I felt I may have a second chance with a follow-up single, after all.”

Penn signed on to direct the music video for her second single, “Dance With the One That Brought You.”

Twain appreciated Penn as a partner

Twain went on to discuss just how lovely of a collaborator Penn was, and how focused he was on making the music video a success.

“He was very cool and fun, direct with his ideas but easygoing and open to my input,” she said. “He took the project very seriously, so before I knew it, I was at a Los Angeles film studio shooting the video for ‘Dance with the One That Brought You.'”

“To be honest, the song, a midtempo number, wasn’t very strong, and I regret that Sean’s ability and enthusiasm were wasted on a track that I knew was never going to amount to much commercially, but the experience of working with him was incredible,” she continued. “He’d pulled in noted character actor Charles Durning to play the role of the overage good-time Charlie who goes out two-steppin’ with his loving wallflower wife on a small-town Saturday night. I adored him as an actor and even more in person. He was such a sweet man and very gracious toward me.”

Penn helped Twain out when she was in a tight spot, and she’s forever grateful to the actor for assisting her at a time when she needed it. “To me, Sean came across as someone who cared about the underdog,” she said honestly. “It seemed that he listened more than he spoke but was not afraid to speak his mind. A real straight shooter.”