In addition to acting, Raymond was also a singer, composer, screenwriter, director, producer, and decorated military pilot.

He attended the Professional Children's School while appearing in productions like Rip Van Winkle and Mrs. Wiggs of the Cabbage Patch.

His most notable films, mostly as a second lead actor, include Red Dust (1932) with Jean Harlow and Clark Gable, Zoo in Budapest (1933) with Loretta Young, Ex-Lady (1933) with Bette Davis, Flying Down to Rio (1933) with Dolores del Río, Fred Astaire and Ginger Rogers, I Am Suzanne (1934) with Lilian Harvey, Sadie McKee (1934) with Joan Crawford, Alfred Hitchcock's Mr. and Mrs. Smith (1941) with Carole Lombard and Robert Montgomery, and The Locket (1946) with Laraine Day, Brian Aherne, and Robert Mitchum.

[3] In the 1950s he worked primarily in television, appearing in Playhouse of Stars,[4] Fireside Theatre, Hollywood Summer Theater and TV Reader's Digest.

In the 1970s he appeared on ABC Television Network's Paris 7000 and had guest roles in The Outer Limits, Robert Montgomery Presents, Playhouse 90, G.E.

[7] He served as an observer aboard B-17 anti-submarine flights along the Atlantic coast before attending intelligence school and shipping out to England in July 1942.

[10] He met her at a Hollywood party two years earlier at Roszika Dolly's home;[11] MacDonald agreed to a date, as long as it was at her family's dinner table.

[11] Despite the strong relationship, Raymond's mother did not like MacDonald, attempting to snub her a few times (such as arranging her son with Janet Gaynor as a plus one at a charity ball),[12] and did not attend the wedding.

[10] The Raymonds lived in a 21-room Tudor Revival mansion named Twin Gables with their pet dogs, birds and their horse White Lady, which Raymond gave to MacDonald as a birthday present;[13] after MacDonald's death, it was briefly owned by John Phillips and Michelle Phillips from The Mamas and Papas.

"[16] When she reunited with Maurice Chevalier in 1957, he asked her why she had retired from films, to which she replied, "Because for exactly twenty years I've played my best role, by his [Raymond's] side.

Despite rumors of getting close with Jane Wyman,[8] in 1974, Raymond married Nelson Bentley Hees and they lived together in Pacific Palisades.

[3] Raymond devoted time to Jeanette MacDonald's International Fan Club, befriending president Clara Rhoades, and taking a few members out to lunch annually.

She writes of verbal abuse from Raymond, physical neglect, and being left alone for 44 days during the year until the diary ends on November 1, 1963, the date she flew to Houston Methodist Hospital for heart surgery.