Oklahoma lad grows up to become America's favorite humorist.

In 1900, in Oolagah, Oklahoma Indian Territory, congressmen are meeting at the house of Clem Rogers, a prominent citizen of Oklahoma and the Cherokee nation, to decide on Oklahoma statehood. Meanwhile, Betty Blake meets Will Rogers, a cowpoke returning home after two years of drifting, while she is helping her brother-in-law, station master Dave Marshall, at the train station. Betty ignores Will's friendly advances, but later learns that he is the son of Clem, who is anxious that Will take his place in the community. Clem wants Will to run their ranch, but Will is happiest meeting people and doing rope tricks, and his management style is too easygoing for Clem. Two weeks later, Betty sells Will and his friend, Dusty Donavon, two one-way tickets out of town. Through postcards that Will sends her, Betty learns that Will and Dusty sign up with a Wild West Show in South America and make a worldwide tour. When the troupe performs at the 1904 St. Louis World's Fair, Betty attends, and after the show, Will proposes to her. Although Will has talked of settling down, Betty learns on a train to Niagara Falls that both Dusty and Will's horses are accompanying them, as Will has signed on with a traveling show to finance their honeymoon. Almost one thousand performances later, Will and the pregnant Betty are planning to return to Oolagah, when Will is written up in a newspaper for lassoing a dangerous bull that got loose during a performance at New York City's Madison Square Garden. Seeing the article, Bert Lynn, a theatrical agent, offers Will a job at Oscar Hammerstein's Victoria Theater on Times Square, but Will's rope tricks, performed astride his horse, do not transfer well to vaudeville, and his act is soon canceled. After six months of unemployment and with the baby almost due, Will is offered a job at a Brooklyn theater as a last-minute fill-in performer, but Dusty and the horse are delayed, so Will begins his act alone. As he fumbles with his rope and chatters nervously, the audience finds Will's self-effacing, down-home presence appealing, and a new comedy act is born that night, as well as his first child. Soon he is headlining with Eddie Cantor at the Ziegfeld Follies, where he adds humorous political commentary to his act, poking fun at all sides of an issue. Believing that Will's morale-building humor expresses the heart of the American people, President Woodrow Wilson urges Will to write, but Will is uncomfortable being taken seriously. A few years later, Will buys a ranch for Betty and their three children in Santa Monica, California, and works in films. Clem shows up at the ranch, urging Will to create more than pie-in-the-face comedies, and even Betty urges Will to use his influence and humor responsibly. After meeting Wiley Post, an airplane pilot and fellow Cherokee, Will learns to fly and becomes a supporter of General Billy Mitchell's campaign to develop aviation for national defense. When Mitchell is charged with insubordination, Will begins a public speaking tour in support of the general that makes people laugh, as well as think. Will also begins writing a syndicated newspaper column and later, makes a European tour, finding himself welcomed by heads of state and the common people. When he returns, the United States is hard hit by the Depression, and Will is troubled to see his childhood neighbors and friends leave Oolagah to find work in the cities. After getting financial support from John D. Rockefeller and Henry Ford, Will gathers celebrities such as Fanny Brice, Marilyn Miller, Al Jolson and Eddie Cantor to throw "monster benefit" relief performances all over the country. For months, working long hours, Will flies across the country to build morale and make money for those in distress, with Wiley as his pilot. When election time rolls around, both Democratic and Republican parties adopt a relief platform, and at the Democratic National Convention, Will is nominated as a "favorite son." During his speech in support of Franklin D. Roosevelt, Will, who is honored to be "accepted by the people he comes from," tells the crowd, "I never met a man I didn't like." Witnessing the event, Clem, an Oklahoma senator, finally realizes that Will's gift to uplift and teach using humor is an important accomplishment. Later, Betty watches Will take off with Wiley for Alaska to back an appropriation bill for Alaskan defense, and has an ominous premonition, as Will has Wiley circle the plane to wave one last goodbye.