How I Learned to Love the Bootboys received generally favourable reviews from critics, some of whom praised the quality of the songs, while others commented on the nostalgia aspect.
As Haines struggled for a new direction, he opted to play with his friend Ian Bickerton in the folk act Balloon, where he met John Moore and Sarah Nixey.
He expanded on this, detailing that the decade consisted of "black and white TVs and the power going off every Saturday night ... And closedown and the bloody national anthem at the end of it".
[9] It was split into two parts, an experimental side and a pop-sounding one, to which Haines regretted not putting more material on it, such as the B-sides "Get Wrecked at Home" and "Breaking Up", to expand it into a double album.
[2] Sunday Herald's Neil Cooper wrote that the title was a homage to the "1990s vogue for all things laddish and the laughable re-invention of classroom geeks as lager-swilling football yobs"; Haines said he was "not a team player and I certainly wouldn't get involved with rough boys".
[9] Clarence Tsui of South China Morning Post wrote that there was "deadpan tales of incestuous fathers, wily street gangs and the despairing rise of right-wing nationalism are set to 1970s and 80s grooves" amongst the lyrical themes found on the album.
[10] The album's opening track "The Rubettes" is a Brill Building[11] tribute to the band of the same name,[12] incorporating that act's song "Sugar Baby Love" (1974).
[7] Louder Than War's Craig Chaligne wrote that both "The Rubettes" and "1967" detailed "characters with polar opposite attitudes towards pop music but both finishing with a reference to the nineties".
[14] "How I Learned to Love the Bootboys" is a quiet track, with hushed vocals from Haines, that is joined by the sound of sirens, a dub bassline and electro noises.
[11] The chorus of "Some Changes" evokes "Heroes" (1977) by David Bowie; "School" sees Haines sing from the viewpoint of a child in the process of being abducted over a start-stop drum pattern.
[12] How I Learned to Love the Bootboys was released by Hut Records on 5 July 1999; it was promoted with one-off performance from the Auteurs at the Embassy Rooms in London 11 days later.
[21] How I Learned to Love the Bootboys was then included on the career-spanning CD box set People 'Round Here Don't Like to Talk About It – The Complete EMI Recordings (2023) alongside the other Auteurs albums.
[11] Tudor called it a "daring return to form" after the "intriguing diversion" of the Baader Meinhof project, adding that it was a "more successful and accessible collection of songs and stories than its recourse to glam-stylings might suggest".
[29] In a review for The Times, journalist Nigel Williamson noted that Haines focused on the "banality of the Seventies", but felt that the tracks "lack[ed] wit and far from being subversive are simply arch".
[25] David Sinclair of The Times said that Haines "complains in a querulous half-croak, half falsetto voice that he hates nostalgia, and then indulges in a succession of musty tales from a troubled past ...