[4] His other hit singles include "Vincent", "Dreidel", "Castles in the Air", and "Wonderful Baby", as well as renditions of Roy Orbison's "Crying" and the Skyliners' "Since I Don't Have You".

By age 16, he had bought his first guitar and began making contacts in the music business, becoming friends with the folk singers Erik Darling and Fred Hellerman of the Weavers.

Fulfilling his father's request,[8] McLean graduated from Iona Preparatory School in 1963,[9] and briefly attended Villanova University, dropping out after four months.

After leaving Villanova, McLean became associated with the famed folk music agent Harold Leventhal for several months before teaming up with his personal manager, Herb Gart.

For the next six years, he performed at venues and events including The Bitter End and the Gaslight Cafe in New York, the Newport Folk Festival, the Cellar Door in Washington, D.C., and the Troubadour in Los Angeles.

Following Gart's death[10] in September 2018, McLean wrote: I feel it is important to note that Herb did many good things for me in the beginning but could not deal with my success, as odd as that may sound.

In about 1982 Herb told me his associate Walter Hofer who ran Copyright Service Bureau (a collection business for song publishers) had stolen $90,000 from my account but had "put it back".

[12] He turned down a scholarship to Columbia University Graduate School in favor of pursuing a career as a singer-songwriter, performing at such venues as Caffè Lena in Saratoga Springs, New York and The Main Point in Bryn Mawr, Pennsylvania.

Later that year, with the help of a grant from the New York State Council on the Arts, McLean began reaching a wider audience, with visits to towns up and down the Hudson River.

[13] 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.

American Pie's 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" reached number one on the Billboard Hot 100 from January 15 to February 5, 1972, and remains McLean's most successful single release.

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.

[21] 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 and the National Endowment for the Arts.

[22] In the sale catalogue notes, McLean finally revealed the meaning in the song's lyrics: "Basically in American Pie things are heading in the wrong direction.

"[citation needed] 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.

Don brought so much to the project that all I really had to do was capture what he did, and complement it properly when necessary.In 1977 a brief liaison with Arista Records that yielded the album Prime Time, and in October 1978, the single "It Doesn't Matter Anymore".

In 1992, previously unreleased songs became available on Favorites and Rarities, and Don McLean Classics featured new studio recordings of "Vincent" and "American Pie".

[43] 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".

[48] 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".

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.

[58] "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 Ye by name.

[citation needed] McLean's albums did not match the commercial success of American Pie, but he became a major concert attraction in the United States and overseas.

[62] During 2018, McLean embarked on a world tour with concerts in North America, UK, Ireland, Belgium, Switzerland, Germany, Israel, Norway and Finland.

His concert at the London Palladium was reviewed positively by The Times:[63] "His masterpiece ("American Pie") remains one of the great achievements of the singer-songwriter era: eight and a half minutes of allegory, reflection and melody documenting the history of rock'n'roll and the death of 1950s innocence.

– Marilynn Kingwell, The TimesThe Jerusalem Post noted that "McLean was the consummate professional in presenting his master class of the Great American Songbook" in their review of his June 2018 Tel Aviv concert.

[80] In March 2017, McLean's single "American Pie" was designated an "aural treasure" by the Library of Congress, "worthy of preservation" in the National Recording Registry "as part of America's patrimony".

"[84] On November 7, 2019, McLean returned to New Rochelle to view a new mural depicting a likeness of his younger self, with lyrics from "American Pie", on the side of a building on the corner of 134 North Avenue and Bonnefoy Place, painted by artist Loic Ercolessi for a non-profit organization, Street Art for Mankind.

They gathered at the Surf Ballroom in Clear Lake, Iowa, where her brother (and Buddy Holly and the Big Bopper) had their last performance before the plane crash.