When Charlie Brown complains about the overwhelming materialism that he sees amongst everyone during the Christmas season, Lucy suggests that he become director of the school Christmas pageant. Charlie Brown accepts, but it is a frustrating struggle. When an attempt to restore the proper spirit with a forlorn little fir Christmas tree fails, he needs Linus' help to learn the meaning of Christmas.

Charles Schulz's classic comic strip Peanuts started in 1950. Fifteen years later, A Charlie Brown Christmas debuted. When The Little Christmas Special that Could proved to be an unexpected success, the stage was set for successive television specials. To date, over forty have been made. The Charlie Brown specials focus on one round-headed kid, his goofy but intelligent beagle, and their vast array of friends. Each has distinctive qualities: Lucy, the crabby, self-proclaimed psychiatrist; Linus, the blanket-toting theologian; Schroeder, the Beethoven worshiper whose black piano keys are only painted on; Peppermint Patty, the tomboy whose affections toward "Chuck" are only outweighed by her sports abilities; and so on. The wit, the charm, the pleasantness of these specials make them appropriate not just for children, but for the whole family.

After their humiliating 999th defeat, Charlie Brown's whole baseball team quits on him. All seems lost...until Charlie Brown learns that his team can join the Little League and become an official team with real uniforms! But as the team's enthusiasm sparks, Charlie Brown learns that neither girls nor Snoopy would be allowed to play. Charlie Brown faces the difficult decision of breaking this horrible news to his excited team.

This documentary goes behind-the-scenes with Peanuts creator Charles M. Schulz. This film paved the way for the future success of the Peanuts animated television specials, bringing together for the first time Schulz, animator Bill Melendez, producer Lee Mendelson, and composer Vince Guaraldi.