1. 'Citizen Kane' – 1941
The movie that started it all, while at the same time contributing to his decline, Citizen Kane was a once-in-a-lifetime film that consistently ranks at the top as the greatest movie ever made. After his infamous War of the Worlds broadcast in 1938, Welles was called to Hollywood, where he was given carte blanche to make any movie he wanted, which proved to be both a blessing and a curse. Following some fits and starts, the result was Citizen Kane, a bold and technically brilliant examination of the rise and fall of one Charles Foster Kane (Welles), a once-idealistic newspaper publisher whose dying word, "Rosebud," is investigated by a dogged reporter. The reporter interviews those who knew, and often loathed, Kane and uncovers many facets of his increasingly lonely life. Despite being hailed by critics, real-life newspaper magnate William Randolph Hearst—Welles' inspiration for Kane—went on a rampage to squash the film prior to release, which helped make Citizen Kane a box office flop. The film earned nine Oscar nominations, including Best Picture and Best Director, but lost out to John Ford's How Green Was My Valley, presumably due to fear of a Hearst backlash among Oscar voters.
2. 'The Magnificent Ambersons' – 1942
Despite the financial failure and controversy surrounding Citizen Kane, Welles charged full steam ahead with his next picture, The Magnificent Ambersons, an adaptation of the novel by Booth Tarkington. While drawing from the same technical innovations employed in Kane, Welles told a much more straightforward narrative with this multi-generational look at a wealthy, old money family slipping into obscurity in the face of unrelenting progress. Starring Joseph Cotten, Dolores Costello, Ann Baxter, Tim Holt, and a brilliant Agnes Moorehead, The Magnificent Ambersons proved to be another massive headache for both Welles and his home studio, RKO Pictures, the latter of which took control of the final edit after the director came in over shedule and over budget. RKO shaved a good 30-40 minutes off Welles' initial cut, whittling it down to a brief 88 minutes. Naturally, Welles was furious and fought unsuccessfully to regain control of the picture. Decades later, Welles was still emotionally stricken by having his film taken away, even though by then it was considered an all-time classic.
3. 'The Lady from Shanghai' – 1948
By this point in his career, Welles had a reputation for being an enfant terrible, but that didn't prevent him from once again stepping behind the camera to direct the stylish film noir, The Lady from Shanghai, which starred Welles opposite his soon-to-be ex-wife, Rita Hayworth. Welles starred as Michael O'Hara, an Irish sailor who saves the beautiful, but mysterious Elsa Bannister (Hayworth) from a robbery in Central Park. Turns out she's the wife of famed defense attorney, Arthur Bannister (Everett Sloane), but that doesn't stop O'Hara from falling in love with Elsa after being offered a job. That proves to be a fateful mistake, as O'Hara is pulled into a web of lust, intrigue, deceit, and murder. Plagued by production delays and a poorly tested rough cut that stretched to 155 minutes, The Lady of Shanghai spent years, even decades being seen as one of Welles' greatest failures, though later generations have elevated it to one of the prime examples of great film noir.
4. 'Othello' – 1952
After the failure of The Lady of Shanghai, Welles was forced to operate outside the studio system and embarked on directing a trilogy of Shakespeare adaptations. He failed miserably with his low-budget take on Macbeth, but fared much better—critically, at least—with his version of The Bard's Othello, the making of which involves one of the most bizarre tales in motion picture history. Three years in the making, Othello was shot with on a bare bones budget largely fueled by money Welles earned from acting in other people's films. Once that money ran out, Welles would shut down the picture in order to refill the coffers until finally finishing principal photography in 1951. From there, Welles struggled with the audio and post-production, and thanks to little funds he was never able to fully correct the problems. Welles briefly basked in glory when Othello won the Palm d'Or at the 1952 Cannes Film Festival, but was hit hard by critics in the United States. Finally, in 1992, Welles' daughter, Beatrice, spearheaded a digital restoration that took just as long to complete as the original film. This time, however, critics hailed the film, calling it one of the finest adaptations of Shakespeare ever committed to film.