(Credits: Far Out / YouTube Still)
Mon 23 March 2026 8:00, UK
When she was at the height of her fame in the late 1980s, a lot of people would have given their arm to be seen walking around town with Madonna.
Madonna was seen as something of a sex symbol at the time, and while a large amount of this was done in a way that was very typical of the male gaze forcing this upon audiences at the time, which some would argue would test the limits of acceptable behaviour today, it’s still clear that a figure like her would be able to capture attention in any era.
She played into this though, essentially trying to reclaim her sexuality and make it female-centred in a way that was revolutionary, and some of her music videos and stage attire, as raunchy as they were, were praised for how she was the one in control of her image, and how she wanted to spread a sex-positive image while also being a figure who people swooned over.
While she was an incredible pop star, there were plenty of discussions over whether she would stand a chance of flirting with other aspects of the entertainment industry as well, and given how many musicians have ended up making a transition into cinema over the years, there was absolutely no reason why Madonna couldn’t do the same.
She ended up appearing in plenty of films in the 1980s and ‘90s, but could have been in much higher demand had she been active in an earlier decade when this crossover was a more prominent feature within the entertainment industry.
During a 1989 interview with Rolling Stone she was asked about whether she regretted the fact that she wasn’t as embedded in Hollywood, which she had some reservations about, but at the same time, was asked which stars of the past she would have wished to have brushed shoulders with, which she took as an opportunity to share her love for one particular icon of the silver screen.
“Oh, Jimmy Stewart,” she responded. “I love him so much. I would die to meet him! I can think of two incredibly favorite moments in his films that just melt me. In It’s a Wonderful Life, there’s that scene where he’s standing with Donna Reed, who’s talking on the phone, and he’s telling her that he doesn’t love her as he’s kissing her, and he’s crying. Clearly, he loves her so much.”
She then went on to describe the other scene in which he steals the show, and the way she would have absolutely loved to have been on the receiving end of his suave charm. “The other moment is in Rear Window when he gives Grace Kelly this look,” she added. “She’s spending the night with him, and he turns and rests his chin on the back of a chair and looks at her so lovingly, I can’t describe it, but that is the way I want someone to look at me when he loves me… It’s the most pure look of love and adoration. Like surrender. It’s devastating.”
A true Hollywood icon, and probably high up on everyone’s list of stars they’d love to meet, James Stewart is undoubtedly one of the greats in film, and who knows – had Madonna been around in previous decades to flaunt her talents, perhaps she would have been exactly the right fit to star alongside Stewart in one of his many roles.
