This drink sounds more like food than drink and it does originally derive from the cake, but it was given it’s name during the short era of naming drinks after cakes. Here is an early printing of this drink:
Complete world bartender guide – Page 409 by Bob Sennett in 1993
“Pineapple Upside-Down Cake – Amaretto Di Saronno, cream, grenadine, and pineapple juice”
This drink is the first of it’s era and might even be considered a sub-trend of the “cookie” era. It shortly followed and slightly spilled into the trend of naming drinks after cookies, but it appears the cookie drinks began to fade as the cake drinks popularity rose. This drink spawned drinks such as the carrot cake, apple pie, cheesecake, and the popular chocolate cake.
The vodka introduction to this drink began in the mid-late 1990’s, likely introduced after stoli vanil or absolut vanilla. This drink does not appear to contain vodka up until this point. The vanilla flavor does give a more noticable similar flavor to the drinks name because of it’s cream base, but it is important we do not forget what these drinks originally contained.
This drink conforms to it’s stereotype of either being layered or spirit only in the case of the cookie/cake eras. This drink is served pousse-cafe style and was originally served as a shot, another common trend of the era.
This drink dates between 1984 – 1991 and contained at least as of then:
Layer ingredients in this order:
Shake and strain these ingredients in to a shot glass, prior to layering the remaining ingredients:
Amaretto (Di Saronno is mentioned as early as 1993)
Layer these ingredients:
Grenadine (Will sink to the bottom)
Vanilla-flavored Vodka (Modern, Stoli Vanil is mentioned as early as 2006)