Given the name of this drink you would think it belongs to the classic transportation era and was created during the 1950's, 1957 to be more precise. However, this drink belongs to the southern comfort era and is much more recent than you may believe. Here is an early printing:
Ultimate Juicing: Delicious Recipes for Over 125 of the Best Fruit ... by Donna Pliner Rodnitzky in 2000
"'57 Chevy What a cool way to bring back the good old days of the fifties. 1 SERVING 21⁄2 cups cubed pineapple 2 tablespoons vodka 2 tablespoons Grand Marnier 2 tablespoons Southern Comfort Place the pineapple in the juicer"
This drink appears in literature rarely prior to 2000, and suddenly explodes into modern american drinking culture as seen in these publications:
Library journal: Volume 127, Issues 10-13 by William White in 2002
"The best disc of the bunch is BarBack, with its huge file of drinks ranging from a '57 Chevy (vodka. Southern Comfort, Grand Marnier, and pineapple juice)"
The professional bar & beverage manager's handbook: how to open ... - Page 18 by Amanda Miron, Douglas Robert Brown in 2006
"57 Chevy 747 1⁄2 oz Irish crème liqueur 1⁄2 oz amaretto 1⁄2 oz Kahlua Pour and serve ingredients."
The Vodka 1000: The Ultimate Collection of Vodka Cocktails, ... - Page 5 by Ray Foley in 2007
"'57 CHEVY 2 oz. Skyy vodka 1 oz. pineapple juice 1 oz. Grand Marnier 1 oz. Southern Comfort Shake and serve."
This drink dates between 1995 and 1999 and contained at least as of then:
Shake these ingredients:
Strain into an ice filled highball glass.