In the Greater Boston area he formed The Modern Lovers, a proto-punk garage rock band. Other notable members of the group were keyboard player Jerry Harrison and drummer David Robinson, who later joined Talking Heads and The Cars, respectively. In 1972 they recorded a series of demos with producer John Cale (formerly of Velvet Underground).
Among these songs were the seminal "Roadrunner" and "Pablo Picasso" which were eventually released on the group's post-breakup album, Modern Lovers (1976). The album was unique for its time, featuring Velvets-influenced basic three-chord rock ("Roadrunner" - based on just two chords - is a clear homage to "Sister Ray") at a time when glam and progressive rock were the norm.
Later in 1972 the group also recorded with producer Kim Fowley; these demos were eventually released in 1981 as The Original Modern Lovers. Despite playing live regularly, the Modern Lovers had a difficult time securing a record deal. By late 1973, Richman wanted to scrap the recorded tracks and start over with a mellower, more lyrical sound, influenced by the laid-back local music he had heard when the band had a residency at the Inverurie Hotel in Bermuda earlier in the year. This stymied efforts to complete a debut album, and led to the breakup of the original Modern Lovers in February 1974.
In 1975, Richman moved to California to record as a solo singer/songwriter with Beserkley Records. His first released recordings appeared on 1975's Beserkley Chartbusters compilation, where he was backed by members of Earth Quake and the Rubinoos; these four songs also appeared on singles on the independent Beserkley label.
In early 1976, Richman put together a new version of the Modern Lovers, but all the members were different. The new incarnation were essentially his backing band, and were billed as Jonathan Richman and the Modern Lovers. The albums produced by the new group found Jonathan turning away from electric rock music towards gentler acoustic textures, with a strong rooting in 50s rock and roll (Chuck Berry's "Back in the USA" was part of his repertoire at this time), while his lyrical focus became more self-consciously childlike and naive. The album, Jonathan Richman and The Modern Lovers, was released in January 1977, Rock and Roll with the Modern Lovers followed a month later, and Modern Lovers Live in 1978.
In Great Britain, Richman was recognised as a progenitor of the punk rock scene, and several of his singles became hits - "Roadrunner" reached Number 11 in the UK pop charts, and its follow-up, the instrumental "Egyptian Reggae", made Number 5 in late 1977. "Egyptian Reggae" was a version of Jamaican musician Earl Zero's reggae song "None Shall Escape the Judgment"; Zero was credited as co-writer on Richman's later versions of the track.
1979's Back in Your Life was released under the "Jonathan Richman and the Modern Lovers" moniker, but only about half the disc featured a backup band — the rest was solo work. This album was probably the most extreme detour by Richman into eclecticism; after the traditional acoustic rock of the previous albums, this one's solo tracks showed off a string bass and glockenspiel as main instruments.
Richman went on sabbatical for a few years staying in Appleton, Maine and playing at a local diner in Belfast,Maine, called Barb's Place. He returned in 1983 with Jonathan Sings!, followed by "Rockin' and Romance" (produced by Andy Paley and engineered by Daniel Levitin). These were followed up with a series of pop efforts (It's Time for Jonathan Richman and the Modern Lovers, and Modern Lovers 88 from 1985, 1986 and 1988 respectively). After the latter release, the "Modern Lovers" moniker was finally retired, and having begun a true "solo" career, he returned to swooping madly around the musical landscape: country music with 1990's Jonathan Goes Country, and Spanish translations of his earlier work (as well as traditional Spanish songs) with Jonathan, Te Vas a Emocionar! (1993)
In 1994 a cameo in the SNL spin-off film It's Pat was left on the cutting-room floor.
Another major profile boost was a key part in the Farrelly Brothers hugely successful 1998 film, There's Something About Mary, where he played half of a two-man Greek chorus that commented on the plot while performing in the framed action itself - Jonathan is shot at the end of the movie. He also appeared briefly in a bar scene in a previous Farrelly Brothers film, Kingpin.
He has continued his release schedule all along, with You Must Ask the Heart (1995), Surrender to Jonathan (1996), I'm So Confused (1998), Her Mystery Not of High Heels and Eye Shadow (2001), and. In 1998 a live album of Modern Lovers recordings from the early 1970s was released, Live at the Long Branch & More. There is also a DVD of a live performance Take me to the Plaza (2002).
In live 'solo' shows, he frequently tours with drummer Tommy Larkins, the other part of the two-man chorus mentioned above. Richman makes use of the flexibility allowed by the two-man format to keep his shows loose and spontaneous, frequently punctuating his songs with extemporaneous ruminations on life and love, on-the-spot transpositions of songs into any of five languages (English, Spanish, French, Italian and Hebrew), and unaccompanied dancing.
In 2003, Richman married Nicole Montalbano of Chico, California.She contributed backing vocals to the album Not So Much To Be Loved As To Love (2004).
Richman's music has set the tone for many quirky college rock acts like Violent Femmes, They Might Be Giants ("Roadrunner" reportedly inspired John Flansburgh to become a musician), Weezer, Tullycraft, Jens Lekman, singer Frank Black (who composed the tribute song "The Man Who Was Too Loud"), Art Brut, and Nerf Herder who composed a song about him, titled "Jonathan". It appeared on the band's second album How To Meet Girls.
"Roadrunner" is on the soundtrack of School of Rock. In the commentary, director Richard Linklater mentions it is often called "the first punk song" and wanted to include it for that reason, along with all the other seminal rock songs in that film.
A tribute album, If I Were a Richman: a Tribute to the Music of Jonathan Richman, was released by Wampus Multimedia in 2001.
(These three live albums are from the same three 1971-3 performances, but add and subtract a few different songs. The last two, combined, contain all the songs).