How Many More Years Midnight", described by Phillips as "the most different record I ever heard", was probably recorded at a different session. Phillips had not yet set up Sun Records and regularly leased his recordings to the Chess label in Chicago. The record was issued as Chess 1479 on 15 September 1951, with "Moanin' at Midnight" as the A-side and "How Many More Years" as the B-side. "Moanin' at Midnight" entered the R&B chart on 10 November 1951, and was followed four weeks later by "How Many More Years", which became the more popular side and rose to no.4 on the chart. The
How Many Licks? and a bling accessary". Lil' Kim and Sisqó also exchange pick-up lines during the song. The chorus refers to the advertising slogan for Tootsie Pops ("How many licks does it takes to get to the Tootsie Roll centre of a Tootsie Pop?"), and ties sexuality to consumerism according to media studies professor Scott Wilson. For the track's remix, Lil' Kim associates her rapping abilities with oral sex: "Ya neva seen this stroke of genius / [I] put tha cleanest, meanest lips on ya penis!" She is also noted to popularize the word "gangstress" which she had previously used in "Spend