Pleased to Meet Me was the only album recorded by the band as a trio. After their previous album Tim, Bob Stinson was either kicked out of the band (ostensibly for problems with drugs and alcohol, though most of the other Replacements also had serious substance abuse problems at the time) or quit on his own volition due to creative differences. Many[who?] have attributed the noticeable shift toward a more accessible American rock and roll sound on Pleased to Meet Me to Bob Stinson's departure. The band recorded the demos for this album in August 1986, while Bob Stinson was still in the band.
The album to some degree maintains the style of the previous album. While the punk roots of the group were still apparent on Tim, by Pleased to Meet Me they were there more in spirit as the band delved into other genres, such as soul and cocktail jazz, alongside tracks featuring their customary hard rocking sound. Perhaps due to the album's recording in soul music center Memphis, Tennessee or the influence of producer Jim Dickinson, the band augmented its sound with saxophone on the tracks "I Don't Know" and "Nightclub Jitters" and with a horn section on "Can't Hardly Wait", which features Big Star vocalist Alex Chilton on guitar. The lyrics and idea for "IOU" were based on an autograph "IOU nothing" that Iggy Pop had given Westerberg backstage several years before.
The album's cover art mocks the band's transition from young punks to successful musicians with a major record deal, depicting a handshake between one person clad in a suit, starched white shirt, glitzy watch and diamond ring and the other wearing a ripped workshirt. The self-mocking tone continues on the song, "I Don't Know", with its chorus, "One foot in the door/The other one in the gutter." The color scheme of the cover art was an homage to the 1960 Elvis Presley album G.I. Blues.
Pleased to Meet Me was critically acclaimed and appeared at number three in The Village Voice's Pazz & Jop critics' poll for 1987.AllMusic reviewer Thomas Erlewine felt that Pleased to Meet Me "was the last time [The Replacements] could still shoot for the stars and seem like their scrappy selves and, in many ways, it was the last true Replacements album".