Following his discovery by producer and manager Mike Hurst, Stevens debuted professionally in the music business with the release of his single "I Love My Dog" in September 1966.

The song's surprising commercial success established his idiosyncratic songwriting style and extended his contract with Deram Records.

"Matthew and Son" entered the Record Retailer chart in January 1967 before peaking at number two in February, becoming Stevens's highest-charting single in his home country.

Stevens has stated that he took inspiritation from his tailor Henry Matthews, who made suits for him, and thought up the story of the worker who is the main character in the song.

[11] As originally recorded by Cat Stevens, "Matthew and Son" is a baroque pop song that was written in a thirty-two-bar form, primarily utilizing the pitches found in the E major key scale.

[20] Journalist Andy Neill compares the lyrical content to that of the Easybeats contemporary hit single "Friday on My Mind" (1966), noting their similar statuses as odes to the working class.

[3][13] "Matthew and Son" was recorded in roughly six or seven takes, with the session also yielding two other songs; "Granny" and "School is Out", the latter of which would become the B-side of his follow-up single "I'm Gonna Get Me a Gun".

[3][20][nb 6] To promote the single, Stevens was in January 1967 called onto various light entertainment television shows, including Ready Steady Go!

[13][22] Elsewhere in Continental Europe, "Matthew and Son" also saw some chart success, which was primarily fueled by Cat Stevens's tour to West Germany in the early months of 1967.

Writing for Disc and Music Echo, journalist Penny Valentine believed that Cat Stevens would become "Britain's up-and-coming songwriter" because of the release.

Fame stated that the record was a "strong double-sider", noting the B-side "Granny" to be as good, and suggested that Stevens "surprised" and made him "completely knocked out".

[48] In Cash Box, the staff reviewer noted the lyrics, considering it to be a "precise, biting social commentary effort", while also praising the B-side.

[49] Retrospectively, "Matthew and Son" has also received praise from critics, with Bruce Eder of AllMusic stating that song's "tinkling harpsichords" was "a beautiful, candid audio "snapshot" of one side of Swinging London's musical ambience in late 1966 and early 1967".

[50] Andy Neill similarly believes that the song and its accompanying album were a testament to both Stevens's idiosyncratic songwriting style and Hurst's ability to "conjure suitably imaginative arrangements".

[13] Because of the single's success, Stevens became part of a package tour together with Jimi Hendrix, the Walker Brothers and Engelbert Humperdinck which according to John Tracy cemented the "healthy reputation his platters had already started to create".

[46] Since its original release, Cat Stevens has also referred to "Matthew and Son" in his other musical work, including a small four-note riff from the song in "(I Never Wanted) To Be a Star" from his album Izitso (1977).

[53][54] Charlesworth also suggests that the song inspired the melody for British pop group Tears for Fears 1982 single "Mad World", which would become a worldwide hit that year.

[55] Stevens himself has acknowledged this influence from the song, and has references this during performances, most notably during his 2016 tour and his surprise appearance at the 2023 Glastonbury Festival.