Norman Rockwell was searching for a train car for his latest painting. The New York Central's Lakeshore Limited Railroad offered him one, the Twentieth Century Limited. However, the artist thought it looked too modern for his painting. A week later, an older car arrived, more appropriate for Rockwell's picture.
Rockwell interviewed three models to play the Pullman porter, but none sufficed. However, along with the new car came a black Pullman porter, a twenty eight year veteran. Many Blacks served as Pullman porters after the Great Migration to the northern cities of the United States. Rockwell also interviewed four boys to play the role of the passenger, settling on his own son, Peter. Peter sat in his seat, hunched over the table, trying to figure out the tip for the Pullman porter.
Leaning against the wall of the train car is a railroad postcard, an attempt by the artist to acknowledge the railroad's generosity in lending him a car. The gesture was the equivalent of $10,000 worth of free publicity for the New York Central Railroad. Boy in Dining Car appeared on the cover of The Saturday Evening Post on December 7, 1946.