Skating waiters, or carhops as they were called then, were the result of a combination of three main factors — the explosion in personal car ownership in America, roller skating as national pastime, and women seeking job opportunities.
Starting back as far as the 1920s, folks were spending more and more time in their cars. Personal car ownership kept going up and up and people were enjoying the freedom and luxury of driving.
Kirby’s Pig Stand in Dallas Texas was the first restaurant to offer “drive in” service in 1921. Many other restaurants soon followed. You could pull up to a diner, go up to a window, order a burger and a shake, and eat in your car. That was living!
To compete, restaurants started offering different incentives to lure you to their site — special menus, flashy neon, and especially “carhops.” Carhops were originally young men in uniform who would take your order from your car and bringing you your food from the kitchen. But during World War II, when most able bodied men were shipped off to the front, young women took on the job. For many young women, this was their first real job opportunity, an important entry point into the world of work outside the home.

But how did skating come in to the role? By the 1940s, roller skating had grown from a child’s pastime into the number one sport practiced in America. At it’s height, there were an estimated 5,000 skating rinks in operation and 18 million skate enthusiasts in the US.
It’s not 100% agreed what was the first restaurant to institute carhops on skates. The chains Sonic and A&W had skating carhops at some of their franchises, but not all. It seems like skating carhops were a novelty, not a common feature. Photos from the era depicts most carhops wearing regular shoes, not skates, on the job.

Like all trends, carhops became less and less common in the 60s and onward. There were various reasons for the decline, but one big one was the birth of a new form of dining — the fast food chain. Ray Kroc, the founder of McDonalds, reportedly described what would differentiate his restaurant chain from others: “no tipping, no jukebox, and no carhops.”
SOURCES
“Building the Black Metropolis: African American Entrepreneurship in Chicago” (2017)
“The Timely Return of the Drive-In Restaurant” Smithsonian Magazine (2002)
“Chicago Rink Rats” Exhibit Showcases the Golden Age of Roller Skating” Chicago Tribune (June 2018)
“The latest US food trend is 1950s nostalgia with the return of carhops” CNN (August 2020)