Early breakthrough McLean recorded
Tapestry in 1969 in Berkeley, California, during the student riots. After being rejected 72 times by labels, the album was released by
Mediarts, a label that had not existed when he first started to look for one. He worked on the album for a couple of years before putting it out. It attracted good reviews but little notice outside the folk community, though on the Easy Listening chart "
Castles in the Air" was a success, and in 1973 "And I Love You So" became a number 1 Adult Contemporary hit for
Perry Como. McLean's major break came when Mediarts was taken over by
United Artists Records, thus securing the promotion of a major label for his second album,
American Pie. The album launched two number one hits in the title song and "
Vincent".
American Pies success made McLean an international star and piqued interest in his first album, which charted more than two years after its initial release.
"American Pie" McLean's "
American Pie" is a song inspired partly by the deaths of
Buddy Holly,
Ritchie Valens and
J.P. Richardson (The Big Bopper) in a plane crash in 1959, and developments in American youth culture in the subsequent decade. The song popularized the expression "
The Day the Music Died" in reference to the crash. The song was recorded on May 26, 1971, and a month later received its first radio airplay on New York's WNEW-FM and WPLJ-FM to mark the closing of
Fillmore East, the famous New York concert hall. "American Pie" reached number one on the
Billboard Hot 100 from January 15 to February 5, 1972, and remains McLean's most successful single release, being certified
six-times Platinum by
RIAA. The single also topped the
Billboard Easy Listening chart. With a total running time of 8:36 encompassing both sides of the single, it was also the longest song to reach number one until
Taylor Swift's "
All Too Well" broke the record in 2021. Some stations played only part one of the original split-sided single release.
WCFL DJ Bob Dearborn unraveled the lyrics and first published his interpretation on January 7, 1972, four days after the song reached number 1 on rival station
WLS, six days before it reached number 1 on WCFL, and eight days before it reached number 1 nationally (see "Further reading" under "
American Pie"). Numerous other interpretations, which together largely converged on Dearborn's interpretation, quickly followed. McLean declined to say anything definitive about the lyrics until 1978. Since then McLean has stated that the lyrics are also somewhat autobiographical and present an abstract story of his life from the mid-1950s until the time he wrote the song in the late 1960s. Once when asked what the song meant, McLean replied that it meant he would never have to work another day in his life. The original
United Artists Records inner sleeve featured a
free verse poem written by McLean about
William Boyd, also known as
Hopalong Cassidy, along with a picture of Boyd in full Hopalong regalia. This sleeve was removed within a year of the album's release. The words to this poem appear on a plaque at the
hospital where Boyd died. The Boyd poem and picture tribute do appear on a special remastered 2003 CD. In 2001, "American Pie" was voted number 5 in a poll of the 365
Songs of the Century compiled by the
Recording Industry Association of America (RIAA) and the
National Endowment for the Arts. On April 7, 2015, McLean's original working manuscript for "American Pie" sold for $1,205,000 (£809,524/€1,109,182) at
Christie's auction rooms in New York City, making it the third highest auction price achieved for an American literary manuscript. In the sale catalogue notes, McLean explained the meaning in the song's lyrics: "Basically in 'American Pie' things are heading in the wrong direction. ... It [life] is becoming less idyllic. I don't know whether you consider that wrong or right but it is a morality song in a sense." The catalogue confirmed some of the better-known references in the song's lyrics, including mentions of
Elvis Presley ("the king") and
Bob Dylan ("the jester"), and confirmed that the song culminates with a description of the
killing of Meredith Hunter at the
Altamont Free Concert, ten years after the plane crash that killed Holly, Valens and Richardson, and that the song broadly depicts how the early rock innocence of the 1950s, and a bygone simpler age, had been lost; overtaken by events and changes, which themselves had been overtaken by further changes.
Mike Mills of
R.E.M. reflected on the song, that "'American Pie' just made perfect sense to me as a song and that's what impressed me the most. I could say to people this is how to write songs. When you've written at least three songs that can be considered classic that is a very high batting average and if one of those songs happens to be something that a great many people think is one of the greatest songs ever written you've not only hit the top of the mountain but you've stayed high on the mountain for a long time." When asked about his record being broken by
Taylor Swift in a
Billboard interview, Don McLean said, "there is something to be said for a great song that has staying power. 'American Pie' remained on top for 50 years and now Taylor Swift has unseated such a historic piece of artistry. Let's face it, nobody ever wants to lose that No. 1 spot, but if I had to lose it to somebody, I sure am glad it was another great singer/songwriter such as Taylor." When Swift broke McLean's record, she sent him flowers and a handwritten note that read "I will never forget that I'm standing on the shoulders of giants".
"Vincent" "
Vincent" is a tribute to the 19th-century Dutch painter
Vincent van Gogh. The inspiration came to McLean one morning while looking at a book about Van Gogh. As he studied a print of Van Gogh's painting
The Starry Night, he realized that a song could be written about the artist through the painting. The song argues that Van Gogh had a psychiatric illness, as opposed to being insane. It reached number 12 on the
Billboard Hot 100 and it proved to be a huge hit worldwide, including reaching number 1 in the UK Singles Chart.
Mike Mills of
R.E.M. said "You can't change a note in that song". In 2018, singer-songwriter
Ellie Goulding recorded a new, stripped back, acoustic guitar-driven version of the song.
Subsequent recordings Personnel from the
American Pie album sessions were retained for his third album
Don McLean, including the producer, Ed Freeman,
Rob Rothstein on bass, and
Warren Bernhardt on piano. The song "The Pride Parade" provides an insight into McLean's immediate reaction to stardom. McLean told
Melody Maker in 1973 that
Tapestry was an album by someone previously concerned with external situations.
American Pie combines externals with internals, and the resultant success of that album makes the third one (
Don McLean) entirely introspective." Other songs written by McLean for the album include "Dreidel" (number 21 on the Billboard chart) and "If We Try" (number 58), which was recorded by
Olivia Newton-John. "On the Amazon" from the 1920s musical
Mr. Cinders was an unusual choice but became an audience favorite in concerts and featured in
Till Tomorrow, a documentary film about McLean produced by Bob Elfstrom (Elfstrom held the role of Jesus Christ in Johnny and June Cash's
Gospel Road). The film shows McLean in concert at Columbia University as he was interrupted by a bomb scare. He left the stage while the audience stood up and checked under their seats for anything that resembled a bomb. After the all-clear, McLean re-appeared and sang "On the Amazon" from exactly where he had left off. Don Heckman reported the bomb scare in his review for
The New York Times titled "Don McLean Survives Two Obstacles". The fourth album ''
Playin' Favorites'' was a top-40 hit in the UK in 1973 and included the Irish folk classic, "Mountains of Mourne" and Buddy Holly's "
Everyday", a live rendition of which returned McLean to the UK Singles Chart. McLean said "The last album (
Don McLean) was a study in depression whereas the new one (''
Playin' Favorites'') is almost the quintessence of optimism." The 1974 album
Homeless Brother, produced by
Joel Dorn, was McLean's final studio recording for United Artists. The album featured fine New York session musicians, including Ralph McDonald on percussion,
Hugh McCracken on guitar and a guest appearance by
Yusef Lateef on flute. The
Persuasions sang the background vocals on "
Crying in the Chapel", and
Cissy Houston provided a backing vocal on "La La Love You". The album's title song was inspired by
Jack Kerouac's book
Lonesome Traveler, in which Kerouac tells the story of America's "homeless brothers" or hobos. The song features background vocals by
Pete Seeger. The song "The Legend of Andrew McCrew" was based on an article published in
The New York Times Joel Dorn later collaborated on the McLean career retrospective
Rearview Mirror, released in 2005 on Dorn's label, Hyena Records. In 2006, Dorn reflected on working with McLean:
Other songs McLean's other well-known songs include the following. • "
And I Love You So" featured on McLean's first album
Tapestry first released in 1970. The song was later recorded by
Elvis Presley,
Helen Reddy,
Shirley Bassey,
Glen Campbell,
Engelbert Humperdinck,
Howard Keel,
Claude François, and a
1973 hit for
Perry Como. The song was performed at the Royal Wedding reception of
Prince Harry and
Meghan Markle in 2018. • "
Castles in the Air", which McLean recorded twice. His 1981 re-recording was a top-40 hit, reaching number 36 on the
Billboard Hot 100 in late 1981. • "
Wonderful Baby", a tribute to
Fred Astaire that Astaire himself recorded. Primarily rejected by pop stations, it reached number 1 on the
Billboard Easy Listening chart. The
American Pie album features a version of
Psalm 137, titled "Babylon". The song is based on a canon by
Philip Hayes and was arranged by McLean and
Lee Hays of the Weavers. "Babylon" was performed in the
Mad Men episode of the same name despite the fact that the song would not be released until 10 years after the time in which the episode is set. In 1981, McLean had an international number one hit with a version of the Roy Orbison classic "Crying". It was only after the record became a success overseas that it was released in the United States. The single hit reached number 5 on the
Billboard Hot 100 in 1981. and in a subsequent re-recording of the song, Orbison incorporated elements of McLean's version. For the 1982 animated movie
The Flight of Dragons, produced by
Jules Bass and
Arthur Rankin, Jr., McLean sang the opening theme. However, no soundtrack has ever been released. Another hit song associated with McLean (though never recorded by him) is singer-songwriter
Lori Lieberman's "
Killing Me Softly with His Song"; Lieberman was inspired by hearing McLean in concert performing his song "Empty Chairs". Afterwards she shared her reaction with her manager,
Norman Gimbel, who had long been searching for a way to use a phrase he had copied from a novel translated from Spanish, "killing me softly with his blues". Gimbel passed the lyrics to his songwriting partner
Charles Fox, who in turn composed the music to "Killing Me Softly with His Song". Lieberman recorded the song (now credited to Gimbel and Fox) and released it in 1972. This initial version was heard by
Roberta Flack, who recorded it with slight changes to create a number-one hit. Two decades later it was recorded by
the Fugees, who had another hit.
Later career The Don McLean Story: Killing Us Softly With His Songs was published in 2007. Biographer Alan Howard conducted extensive interviews for this, the only book-length biography of the often reclusive McLean to date. McLean attended the opening dinner service of ''
Hell's Kitchen''s
eighteenth season as one of the red diners who had their food cooked by the rookies. McLean is credited as a co-writer on
Drake's song "Doing It Wrong", featuring
Stevie Wonder. The song includes lyrics from two McLean compositions – "The Wrong Thing to Do" and "When a Good Thing Goes Bad" – both of which were featured on his 1977 album
Prime Time. In a July 2022 documentary, titled
The Day The Music Died, McLean discussed for the first time in 50 years the meaning of the lyrics in "American Pie". In February 2022, McLean recorded a performance of "Vincent" at the Immersive Van Gogh exhibit in Los Angeles in honor of Van Gogh's birthday and the 50th anniversary of the song. In April 2022,
Tyson Fury teamed up with McLean to remake "American Pie". McLean won six Telly Awards for the
Fury-Whyte fight opening. In June 2022, McLean published a children's book titled
American Pie: A Fable. The story follows the emotional journey of a newspaper delivery boy in the late 1950s who discovers the joy of friendship and music, eventually learning that when you recognize what truly makes you happy, you are never really alone. McLean led a wave of dropouts from the
National Rifle Association of America (NRA) convention after the mass shooting in
Uvalde, Texas, saying it would be "disrespectful and hurtful" to perform days after 19 children and two adults were killed in a mass shooting in the state. McLean was first among performers who announced they would no longer perform at the National Rifle Association's annual meeting in Houston. In October 2022, McLean called rapper
Kanye West an "attention-seeking fool" over his antisemitic rants. McLean, who briefly lived in Israel, said he stood with his Jewish friends. "Lately, a flood of antisemitic invective has been triggered by the ranting of a stupid attention-seeking fool we all know", McLean wrote in the statement that did not mention West by name. "I want to say I stand with my Jewish friends and I stand with the state of Israel. When this kind of thing happens, we should realize why the state of Israel must be respected and protected." McLean lived in Israel on-and-off from 1978 to 1982, and he "grew to love the country and the people. Living there changed [his] life forever."
Oxford Union address (2025) On 9 May 2025, McLean delivered a keynote address to the
Oxford Union, the
University of Oxford’s historic debating society, reflecting on five decades in music and the cultural after-life of “American Pie.” The engagement formed part of the Union's Trinity Term 2025 speaker series, which also featured figures such as
John Legend and
Nile Rodgers. ==Concerts==