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He also joined his family troupe, from 1910, in their vaudeville act, where he was happy not to worry as much about memorizing lines. Nevertheless, he was soon back on Broadway in The Jail Bird in 1910 and continued his stage career with several more plays. The producers gave appendicitis as the reason for his sudden departure. In December of that year, he returned to the stage in The Fires of Fate, in Chicago, but left the production later that month after suffering an attack of nerves about the forthcoming New York opening. He did not achieve success as a painter, and in 1909 he returned to the US. Lionel confirms in his autobiography, We Barrymores, that he and Doris were in France when Bleriot flew the English Channel on July 25, 1909. Lionel and Doris were in Paris in 1908 where their first baby, Ethel, was born.

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In 1906, after a series of disappointing appearances in plays, Barrymore and his first wife, the actress Doris Rankin, left their stage careers and travelled to Paris, where he trained as an artist. In 1905, he appeared with John and Ethel in a pantomime, starring as the title character in Pantaloon and playing another character in the other half of the bill, Alice Sit-by-the-Fire. The Other Girl in 1903–04 was a long-running success for Barrymore. Both were produced by Charles Frohman, who produced other plays for Barrymore and his siblings, John and Ethel. in such plays as The Second in Command (1901) and The Mummy and the Hummingbird (1902), the latter of which won him critical acclaim. He appeared on Broadway in his early twenties with his uncle John Drew Jr. The theater was not in my blood, I was related to the theater by marriage only it was merely a kind of in-law of mine I had to live with.' Nevertheless, he soon found success on stage in character roles and continued to act, although he still wanted to become a painter and also to compose music. He later recounted that 'I didn't want to act. Reluctant to follow his parents' career, Barrymore appeared together with his grandmother Louisa Lane Drew on tour and in a stage production of The Rivals at the age of 15. When Harlow died in 1937, Barrymore and Clark Gable mourned her as though she had been family. Years later, Barrymore developed a fatherly affection for Jean Harlow, who was born about the same time as his daughters. Barrymore never truly recovered from the deaths of his girls, and their loss undoubtedly strained his marriage to Doris Rankin, which ended in 1923.

Doris Rankin bore Lionel two daughters, Ethel Barrymore II (1908 – 1910) and Mary Barrymore (1916 – 1917). Doris's sister Gladys was married to Lionel's uncle Sidney Drew, which made Gladys both his aunt and sister-in-law. He was married twice, to actresses Doris Rankin and Irene Fenwick, a one-time lover of his brother, John. Barrymore graduated from Seton Hall Preparatory School, the Roman Catholic college prep school, in the class of 1891. While raised a Roman Catholic, Barrymore attended the Episcopal Academy in Philadelphia. He attended private schools as a child, including the Art Students League of New York.

He was the elder brother of Ethel and John Barrymore, the uncle of John Drew Barrymore and Diana Barrymore and the great-uncle of Drew Barrymore, among other members of the Barrymore family. Lionel Barrymore was born Lionel Herbert Blythe in Philadelphia, the son of actors Georgiana Drew Barrymore and Maurice Barrymore (born Herbert Arthur Chamberlayne Blythe).