Sean Penn Played A Little-Known Role In Shania Twain's Career

When he's not landing in natural disaster hotspots and popping up in war zones, Sean Penn has played a role — for better or for worse — in many people's careers. Despite Madonna and Penn's trainwreck marriage being tumultuous and allegedly violent, she credits him (and her next ex-husband, Guy Ritchie) for her filmmaking career. "They encouraged me as a director and as a creative person to do what I did," Madonna told the New York Daily News.

Kate del Castillo isn't so grateful for him, though. Penn dragged her into his disastrous Rolling Stone war on drugs debacle. The ensuing El Chapo interview caused trouble for Penn, but it totally ruined del Castillo's career and even her life. "He used me as bait, and then he never protected me," the actor, currently under investigation by the Mexican government, said during an episode of "Red Table Talk: The Estefans" (via People). "[He] risked my life, my parents' life, my sister's life, and everybody surrounding me."

Robin Wright's career wasn't helped much, either. Wright was married to Penn for 14 years, and despite two kids, it was an emotional rollercoaster of a disaster. Wright told Vanity Fair that her career was put on the back burner while Penn lit up the screen and world map. It took her six years to get back on track after landing the co-starring role in "House of Cards." However, Sean Penn played a little-known role in Shania Twain's career and she can't give him enough props.

Before Shania Twain was selling "more than 100 million records worldwide," she was "a struggling artist paying her dues." Still, her future started to look bright after she released her self-titled first album in 1993. That's when Sean Penn arrived on the scene and played a little-known role in Twain's career.

"All of a sudden Sean Penn calls and says, 'I'd love to direct one of your videos,'" she told "Extra." Twain said that when they met in person to discuss the project, Penn thrust $100 into her hand, telling her, "You look like you could use this," which sounds kind of insulting, but Twain admitted that she'd "really needed it" at the time. "It was a really kind thing to do," she said. Penn ultimately directed "Dance With The One That Brought You," the second single from Twain's debut album.

Meanwhile, Penn may have been the first, but there were plenty more famous fans to come, including Adele, who totally fangirled over the country great after noticing her in the audience. "Thank God you had a hat on... I would have self-combusted had I seen it was you. I adore you. I can't believe you came to my show," Adele captioned an Instagram Story of her singing while Twain watched (via E! News). "That was so special," Twain told "Extra" at the People's Choice Awards. "It was cute; it was very sweet of her," she continued.

Harry Styles is also a huge Shania Twain fan. The unlikely couple sang a duet at Coachella 2022. Wearing a shimmering, multi-colored zig-zag dress, and knee-high boots, Twain looked resplendent. Styles? Not so much. The British heartthrob's glittery, sequin skin-tight all-in-one, slashed to the waistband to reveal his hairless pecs, left a lot to be desired. "This was a magical moment for me," Twain told "Access Hollywood," admitting she'd unsuccessfully quizzed Styles about what he'd wear onstage so she could "be in a similar vibe."

Prince was a Twain enthusiast, too. He even asked her to collaborate on a project with him. However, it all went south after the devout Jehovah's Witness didn't impress Twain much by requesting she not cuss in his presence. Prince learned Twain's cowboy boots were made for walking and that's just what she did. "I'm such a huge fan," she told "Access Hollywood." "I regret it now. I should have just done it."

Meanwhile, during the pandemic, Twain was forced to close down her Las Vegas music residency. That didn't stop her from working, though. "I've written four albums over COVID, you know. I was very productive in the songwriting department," she admitted during an interview on the British breakfast show, "This Morning," sharing she'd been so busy that she'd "written an album that hopefully will be out very soon."