Raymond was notorious in Hollywood for being outspoken against the studio system, saying that it was not "living up to expectations".
The only actors that he had faith in were Fred Astaire and Ginger Rogers, two people that he claimed "knew what they were doing".
He was one of the first actors of the time to go freelance, although he admitted that it was mostly to spite the studios.

He also excelled at sports, such as gymnastics and tennis.
George Sidney once called Raymond "the most gorgeous thing the world had ever seen".

Raymond married Jeanette MacDonald in 1937.
He met her at a Hollywood party two years earlier at Roszika Dolly's home; MacDonald agreed to a date, as long as it was at her family's dinner table.
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), and did not attend the wedding.
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; after MacDonald's death, it was briefly owned by John Phillips and Michelle Phillips from The Mamas and Papas.
MacDonald often worried about her husband's self-esteem.
Although she appreciated his support, MacDonald wished that their success was equal; when Raymond turned down her offer to join one of her music tours, she did not feel let down: "Trailing along on my tours would make him 'Mr. MacDonald', a galling label for any self-respecting man.
As it was, he was called 'Mr. MacDonald' often enough to make me admire tremendously his good sportsmanship in taking it on the chin.
Raymond was sometimes mistaken for Nelson Eddy by MacDonald's fans and passersby, which MacDonald later admitted that she never liked either: "Of course we always laughed it off—sometimes Gene even obliged by signing Nelson's name—but no one will ever know the agonies I suffered on such occasions.
More than anything else in the world those days, I wanted to see him receive as much acclaim as I, to spare him these humiliations."
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] side.
And I'm perfectly happy."
The two of them were married for almost 28 years until MacDonald's death in 1965.

Despite rumors of getting close with Jane Wyman, in 1974, Raymond married Nelson Bentley Hees and they lived together in Pacific Palisades.
Hees died from Alzheimer's in 1995.

Raymond devoted time to Jeanette MacDonald's International Fan Club, befriending president Clara Rhoades, and taking a few members out to lunch annually.
His last public appearance was June 27, 1997, at the 60th-anniversary banquet of the Fan Club at Beverly Wilshire Hotel.

He was a Republican and supported Barry Goldwater in the 1964 United States presidential election.

During the time of the Hollywood Blacklist, he and MacDonald did not involve themselves with the HUAC investigations; neither were ever summoned to a hearing (MacDonald openly disagreed with the situation in a radio interview).
Raymond was notorious in Hollywood for being outspoken against the studio system, saying that it was not "living up to expectations". The only actors that he had faith in were Fred Astaire and Ginger Rogers, two people that he claimed "knew what they were doing". He was one of the first actors of the time to go freelance, although he admitted that it was mostly to spite the studios.
He also excelled at sports, such as gymnastics and tennis. George Sidney once called Raymond "the most gorgeous thing the world had ever seen".
Raymond married Jeanette MacDonald in 1937. He met her at a Hollywood party two years earlier at Roszika Dolly's home; MacDonald agreed to a date, as long as it was at her family's dinner table. 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), and did not attend the wedding. 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; after MacDonald's death, it was briefly owned by John Phillips and Michelle Phillips from The Mamas and Papas. MacDonald often worried about her husband's self-esteem. Although she appreciated his support, MacDonald wished that their success was equal; when Raymond turned down her offer to join one of her music tours, she did not feel let down: "Trailing along on my tours would make him 'Mr. MacDonald', a galling label for any self-respecting man. As it was, he was called 'Mr. MacDonald' often enough to make me admire tremendously his good sportsmanship in taking it on the chin. Raymond was sometimes mistaken for Nelson Eddy by MacDonald's fans and passersby, which MacDonald later admitted that she never liked either: "Of course we always laughed it off—sometimes Gene even obliged by signing Nelson's name—but no one will ever know the agonies I suffered on such occasions. More than anything else in the world those days, I wanted to see him receive as much acclaim as I, to spare him these humiliations." 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] side. And I'm perfectly happy." The two of them were married for almost 28 years until MacDonald's death in 1965.
Despite rumors of getting close with Jane Wyman, in 1974, Raymond married Nelson Bentley Hees and they lived together in Pacific Palisades. Hees died from Alzheimer's in 1995.
Raymond devoted time to Jeanette MacDonald's International Fan Club, befriending president Clara Rhoades, and taking a few members out to lunch annually. His last public appearance was June 27, 1997, at the 60th-anniversary banquet of the Fan Club at Beverly Wilshire Hotel.
He was a Republican and supported Barry Goldwater in the 1964 United States presidential election.
During the time of the Hollywood Blacklist, he and MacDonald did not involve themselves with the HUAC investigations; neither were ever summoned to a hearing (MacDonald openly disagreed with the situation in a radio interview).
Gene Raymond