"Should I Do It" was recorded in the first months of 1981 by both Tanya Tucker and the Pointer Sisters for their respective mid-year album releases: Tucker's Should I Do It and the Pointers' Black & White. Although written by veteran C&W composer Layng Martine Jr. - who'd recall "Should I Do It" as an example of how "sometimes...a song just appears in my brain and kind of writes itself fast"[2] - even as recorded by C&W superstar songstress Tucker "Should I Do It" was not considered a standard C&W number: Cashbox magazine described Tucker's version as a blend of "the girl group classic "[Please] Mr. Postman", with a honky tonk piano and a brief doo wop bit".[3] As recorded by the Pointer Sisters the song was a more overt homage to the girl-group hit sound of the early 1960s.[4][5][6][7][8] A chart disappointment for Tucker in the summer of 1981 - stalling at #50 C&W - ,[9] "Should I Do It" as recorded by the Pointers would reach the Top 20 of the Billboard Hot 100 in early 1982 although it would not rank among the group's very biggest hits being a Top Ten shortfall.[10]
Tanya Tucker recorded "Should I Do It" in the sessions for her twelfth studio album - which would be entitled Should I Do It - at the Hollywood Studio the Sound Labs in April 1981.[11][12] Tucker was produced by Gary Klein, a veteran producer of several Pop & C&W acts including Tucker's swain Glen Campbell.[13]
The Tucker/ Campbell May-December romance was perennial tabloid press fodder, with reports, particularly from February 1981, attesting to the romance being a rocky one.[14] Tucker's tabloid profile seemingly undermined her recording career: subsequent to a Top Ten C&W hit: "Can I See You Tonight", in February and March 1981, Tucker's two springtime single releases were both chart disappointments, with "Love Knows We Tried", stalling at #40 on the BillboardC&W chart where the Tucker/ Campbell duet: "Why Don't We Just Sleep on It Tonight", barely ranked at #85.[9]
Released in June 1981 as the lead single from the album of the same name, "Should I Do It" failed to reverse Tucker's chart fortunes: despite spending seven weeks on the Record World Singles 101-150 chart rising as high as No. 131,[18] "Should I Do It" rose no higher than No. 45 on the magazine's Country Singles chart [17] - with a similar peak (No. 50) on the Hot Country Singles chart in Billboard[15] - indicating a lack of support from C&W radio.
"Should I Do It" was one of two songs by Nashville-based composers to be recorded by the Pointer Sisters for their June 1981 Black & White album release, the other being the album's lead single: "Slow Hand" which had reached #2 on the Billboard Hot 100. Like "Slow Hand", "Should I Do It" was recorded by the Pointers with their regular producer Richard Perry so as to barely resemble a standard C&W song: in the case of "Should I Do It" the Pointers turned the song into (Ruth Pointer quote:) "an ode to the early '60s girl groups in the vein of the Shirelles and the Chiffons."[21] The Pointers had a #3 hit in 1980 with "He's So Shy", which had evoked the elements of the late 1950s/early 1960s girl group classics while being a contemporary number. With "Should I Do It", June Pointer (the lead vocalist on "Should I Do It" and "He's So Shy") had sung lead on "a marvelous recreation - as opposed to modernization - of the late '50s/early '60s sound of the all-girl vocal groups."[22]
"Should I Do It" was mentioned as the choice for the second single from Black & White,[23] and at the time of the album's release it was announced that music videos would be shot for both "Slow Hand" and "Should I Do It";[24] "Slow Hand" was promoted via video as the first single. The label then decided to release two other songs as singles from Black and White; "What a Surprise" and "Sweet Lover Man", released in October and November of 1981, respectively. Neither became a significant hit. In December 1981, the label released "Should I Do It" as an unprecedented, at the time, fourth single from a Pointer Sisters album. The song became a major hit, rising to #13 on the US Billboard Hot 100, dated April 3, 1982. This made Black & White the first Pointer Sisters album to spawn two Top 20 US hits. "Should I Do It" also reached #19 on the Billboard Adult Contemporary chart.[10]
Outside of the U.S. and Canada, "Should I Do It" was released in November 1981 as the immediate follow-up single to "Slow Hand" with the single reaching the Top 20 in Australia, Flemish Belgium, and the Netherlands prior to its January 1982 Billboard US Hot 100 debut. "Should I Do It" had its greatest chart impact in Belgium's Flemish Region and the Netherlands with respective peaks of #6 and #12, topping the chart peak in those territories for "Slow Hand" (#22 Belgium and #33 Netherlands).[25][26]
The Pointer Sisters would record another Layng Martine Jr. composition: "I Want to Do It With You", to serve as B-side of their followup single to "Should I Do It": "American Music". (Never featured on a Pointer Sisters' album, "I Want to Do It With You" - as "I Wanna Do It With You" - would become a Top Ten UK hit for Barry Manilow in 1983).[27]