Richard Cromwell earned $75 per week for his work on Tol’able David. Noah Beery, Sr. and John Carradine co-starred in the film. Later, Cohn signed Cromwell to a multi-year contract based on the strength of his performance and success in his first venture at the box-office. Amidst the flurry of publicity during this period, Cromwell toured the country, even meeting President Herbert Hoover in Washington, D.C. Cromwell by then had maintained a deep friendship with Marie Dressler, which continued until her death from cancer in 1934. Dressler was nominated for a second Best Actress award for her 1932 portrayal of the title role in Emma. With that film, Dressler demonstrated her profound generosity to other performers: Dressler personally insisted that her studio bosses cast Cromwell on a loan-out in the lead opposite her — it was another break that helped sustain his rising status in Hollywood. Emma also starred Myrna Loy in one of her earliest screen performances. After production on Emma was completed, Director Clarence Brown tested Cromwell for the male lead in his next feature: The Son-Daughter, which was set to star Helen Hayes. However, the part of the oriental prince ultimately went to Ramón Novarro, and Cromwell never again worked at MGM. Richard Cromwell’s next role in 1932 was on loan to RKO and was as Mike in Gregory La Cava’s, The Age of Consent, co-starring Eric Linden and Dorothy Wilson. Cromwell is also remembered during this period in Hoop-La (1933), where he is seduced by Clara Bow. This film is considered the swan song of Bow’s career. Next, the much in demand Cromwell starred in Tom Brown of Culver that year, as well.

Around this period in his career in the early to mid-30s, Richard Cromwell also did some print ads and promotional work for Lucky Strike brand cigarettes. According to his niece, Joan Radabaugh, Cromwell was a very heavy smoker. Nevertheless, at his home he was always the gracious host, as his niece related, and as such he took great care to empty the ashtrays regularly, almost to the point of obsession. Next up, was an early standout performance by Cromwell in the role as the leader of the youth gang in Cecil B. DeMille’s now cult-favorite, This Day and Age (1933). To ensure that Cromwell’s character used current slang, DeMille asked high school student Horace Hahn to read the script and comment (at the time, Hahn was senior class president at Los Angeles High School). After a promising start, Cromwell’s many early pictures at Columbia Pictures and elsewhere were mostly inconsequential and are largely forgotten today. Cromwell starred with Will Rogers in Life Begins at 40 for Fox Film Corporation in 1935, it was one of Rogers’ last roles and Poppy for Paramount in 1936 wherein Cromwell played the suitor of W.C. Fields’ daughter, Rochelle Hudson. In 1937, he was the young bank-robber in love with Helen Mack and on the lam from Lionel Atwill in The Wrong Road for RKO.

In the late 1930s, Richard Cromwell appeared in Storm Over Bengal, for Republic Pictures, in order to capitalize on the success of The Lives of a Bengal Lancer. Aside from the aforementioned standout roles in Jezebel and The Lives of a Bengal Lancer, Cromwell did another notable turn as defendant Matt Clay to Henry Fonda’s title-performance in Young Mr. Lincoln (1939). During this period, Cromwell was continuing to enjoy the various invitations coming his way as a member of the A-list Hollywood social circuit. According to Bob Thomas, in his biography of Joan Crawford, Cromwell was a regular at the Saturday Night dinner parties of his former co-star Franchot Tone and then-wife Crawford. Other guests whom Cromwell dined with there included Barbara Stanwyck and then-husband Frank Fay, and William Haines and Jimmy Rogers. During the freewheeling heyday of West L.A. nightlife in the late 30s, Cromwell is said by author Charles Higham to have carried on a sometime, though obviously very discreet, affair with aviator and businessman Howard Hughes. In 1939, Cromwell again tried his luck on the stage in a regional production of Sutton Vane’s play Outward Bound featuring Dorothy Jordan as his co-star. The cast of the production at the Los Angeles Biltmore Theater also included Cora Witherspoon and Reginald Denny. Richard Cromwell became ill and died on October 11, 1960 in Hollywood of liver cancer, at the age of 50. He is interred in Santa Ana, California. Cromwell was survived by his four siblings, including Opal Radabaugh Putnam.