The behind-the-scenes dynamics of Hollywood stars often paint a different picture than their public personas, and James Stewart was no exception. While known as the classic nice guy on screen and in the public eye, his private life had its share of scandalous affairs and passionate romances.

In 1949, Stewart married Gloria McLean, but before that, he had a series of high-profile and hushed-up relationships with silver screen icons like Eleanor Powell, Loretta Young, Ginger Rogers, Norma Shearer, and Dinah Shore. However, one of his most intense affairs occurred ten years before his marriage, with none other than Marlene Dietrich, a Hollywood icon known for her sophisticated allure.

Their affair took place during the filming of “Destry Rides Again” in 1939, a screwball Western romp that showcased Dietrich’s versatility as a trampy saloon singer named Frenchie. Behind the scenes, the passion between Stewart and Dietrich was palpable, despite her status as “box office poison” due to previous film flops.

Stewart, still enjoying his bachelorhood, was captivated by Dietrich’s charms, even though she was married to Rudolph Sieber since 1923. Dietrich’s marriage was famously open, allowing her to engage in numerous affairs with both men and women, including notable figures like Errol Flynn, George Bernard Shaw, John F. Kennedy, and Frank Sinatra.

Their affair on the set of “Destry Rides Again” was no secret, as Stewart reportedly became visibly aroused during a passionate scene with Dietrich, much to the dismay of the director and the actress herself when Stewart eventually ended the affair.

The tumultuous nature of their relationship mirrored the passionate and sometimes scandalous lives of Hollywood stars during that era, adding another layer of intrigue to Stewart’s off-screen persona as the quintessential nice guy.