Gilbert had made forty-one films before he got some publicity by starring in the film Heart of the Hills with Mary Pickford. But real stardom was yet to come. It was now the 1920's, the jazz age and Jack was well suited for the times.

It was during this time that Jack signed with MGM. When Irving Thalberg saw Jack as a southern gambler in "Cameo Kirby, he was so impressed that he signed him to a $1500/week contract. Jack was happy to finally be at a studio where it was reported money was not always a first consideration, where he could be considered a serious and competent actor. Under the guidance of Thalberg, Jack felt confident that his future was secure. Even though Jack was interested in being a star, he also liked the behind the camera role and had done some directing writing early on, but acting seemed to be where he could shine.

Thalberg soon signed Gilbert to the film He Who Gets Slapped with Norma Shearer and Lon Chaney. The film premiered in November, 1924 and was a big success. Shortly after, Thalberg decided to put Jack in his first major production, The Merry Widow with Mae Murray. The film was received well and Photoplay said the film would make Gilbert "the greatest of them all".

This was the happiest and most lucrative time in his life. Thalberg was also good at continuing the success by signing Jack to his next film "The Big Parade". This was truly Jack's biggest break yet and sealed his stardom. The reviews were great. The Big Parade, directed by King Vidor is about the life of a doughboy in WWI. It was timely and well done, with Jack at the center. Many say that if there had been an Oscar, Jack would have won it for this role.

Around this time, he began his endless feud with Louis B. Mayer. One day Jack had been discussing a film he wanted to do with Mayer about a young boy who has an affair with the mistress of a dray man who is serving time in prison. Mayer didn't like the idea because the film was about a fallen woman. Mayer said, who wants to see a film about a whore and a nice boy falling in love? Gilbert replied, "your making other pictures with the same theme". Mayer replied with "only someone like you would bring a whore into a story about a mother and her son." Jack replied, What's wrong with that? My own mother was a whore. Mayer, being very sensitive and loving of his mother thought this was a horrible thing for anyone to say about their mother and he lunged forward to sock Jack. Mayer's hatred of Jack would grow more and more as time went on.

Jack was getting to the top and was admired. Men copied his long collars and French cuffs and he made a blue shirt during the day acceptable at a time when it was just not done. He was seen often in the fan magazines and his every move was observed and everything he wore became a trend. Women were attracted to Gilbert and men wanted to be like him. This was also true of Gilbert's heir to the throne of stardom, Clark Gable.

However, more was to come for Jack in the way of stardom with his new co-star and lover, Greta Garbo....

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