Distinguishable by their yellow box and red logo, Red Apple Cigarettes first appeared in 1994's Pulp Fiction, Tarantino's Oscar-winning crime epic starring John Travolta, Bruce Willis, Samuel L. Jackson, and Uma Thurman, who smokes them in the film's show-stopping diner sequence. Throughout the '90s, the brand popped up in Tarantino-related projects like the short film collection Four Rooms, where they were enjoyed by Tim Roth's bellhop, and in From Dusk Till Dawn, the vampire thriller written by Tarantino and featuring the filmmaker in a rare main role. (Oddly enough, as this Entertainment Weekly article points out, the brand was also featured in the 1997 comedy Romy and Michele's High School Reunion, which starred Mia Sorvino, who was dating Tarantino at the time.)
Later in his career, Red Apple also made appearances in Kill Bill, Grindhouse, and The Hateful Eight, suggesting that the company has a long, dark history that dates back to the Civil War. Often the cigarettes just pop up in a character's hand or in the background, like when a Red Apple billboard appears in Kill Bill, but Once Upon a Time… in Hollywood finds the brand taking center-stage for a change. It's fitting that a movie so obsessed with the passed-down, romanticized rituals of drinking and smoking -- think of all those close-ups of ice trays breaking, lighters flicking, and cocktails getting poured -- would end with an in-joke about the preferred tobacco product of the Tarantino-verse. It's even possible to interpret the alternate history shenanigans of the finale as a hallucinatory side effect of the acid-soaked cigarette Pitt smokes right before things go violently off the rails.
Tarantino's genre-splicing, pop-culture-referencing style of filmmaking has always lent itself to self-mythology. It makes sense that Once Upon a Time… in Hollywood, a film that melds the free-wheeling hang-out vibe of '90s classics like Pulp Fiction and Jackie Brown with the more outwardly ambitious historical approach of Inglourious Basterds and Django Unchained, would nostalgically shine a light on Red Apple one more time. When you wander bleary-eyed out of the theater, you might even go looking to buy a pack. As Dalton says in the ad, tell 'em Jake sent you.