The gentle melodies, light arrangements, and romantic heart of the Lettermen's close-harmony pop songs made them quite a successful group during the 1960s, when changing styles and tastes left many older listeners feeling a bit left behind in the music world. Not only was their Capitol Records debut, 1961's "The Way You Look Tonight," a Top 20 hit, it was their first of 20 appearances on the Billboard Hot 100 that also included the Top Ten singles "When I Fall in Love" (1961) and "Goin' out of My Head/Can't Take My Eyes off You" (1967). During their peak, the trio enjoyed a run of over two dozen consecutive releases on the Billboard 200, from their 1962 debut LP A Song for Young Love, which hit a career-high number six, to 1972's Lettermen 1. The group's appeal lasted for many decades beyond this initial commercial success, however, with founding member Tony Butala active in the Lettermen until his semi-retirement in 2019. In the meantime, the group's 1987 holiday album It Feels Like Christmas was still being reissued into the streaming era, 2000's Greatest Movie Hits updated their repertoire, and New Directions 2010 refreshed some of their favorite tunes in the studio with Les Brown, Jr. His Band of Renown. They received a star on the Hollywood Walk of Fame in 2019, with concert tours and annual fan conventions continuing into the following decade.

Formed in 1959 by singer Tony Butala along with two Brigham Young University alumni, Jim Pike and Bob Engemann, the Lettermen recorded without success for about a year until they signed with Capitol Records. The group's first single for the label, a cover of the Jerome Kern-Dorothy Fields standard "The Way You Look Tonight," reached number 13 on the Hot 100 in late 1961. Its follow-up, "When I Fall in Love," which had been a hit ten years earlier for Doris Day, peaked at number seven for the Lettermen in January 1962.

When their full-length debut, A Song for Young Love, arrived in 1962, it went to number six on the U.S. album chart. They followed it up the same year with Once Upon a Time and Jim, Tony, and Bob before issuing College Standards and the live album Lettermen in Concert, both in 1963. Maintaining a near-constant presence on the chart, the following year brought A Lettermen Kind of Love, The Lettermen Look at Love, and She Cried, and their 1965 sets included You'll Never Walk Alone, Portrait of My Love, and The Hit Sounds of the Lettermen. All of these releases landed in the top half of the Billboard 200, with the latter album reaching as high as number 13. They returned with More Hit Sounds of the Lettermen in 1966, a year that also saw A New Song for Young Love and their first seasonal collection, For Christmas This Year. In addition, Capitol released the trio's first compilation, The Best of the Lettermen. Following 1967's Warm, Spring!, which reached the number 31 spot on the album chart, the group closed out the year with the Top Ten LP The Lettermen!!...And Live! Their first studio full-length of 1968, Goin' Out of My Head, climbed to number 13.

Though the group only reached the Top Ten of the singles chart one more time after 1961, with the 1968 medley "Goin' Out of My Head/Can't Take My Eyes Off You" (the same year Jim's brother Gary Pike stepped in for Engemann), their impressive streak on the Billboard 200 continued, and popular concert tours helped keep the group going long after many of their like-minded contemporaries had called it quits. Special Request and Put Your Head on My Shoulder, both from 1968, didn't manage to crack the Top 40 but still made it into the Top 100, and the Lettermen delivered the number 17 album Hurt So Bad in 1969. That year's I Have Dreamed peaked at 74, with the 1970 LPs Traces/Memories and Reflections also landing outside of the Top 40. The same was the case for all three of the group's 1971 studio efforts: Everything's Good About You, Feelings, and Love Book, their final Top 100 album. In 1972, Lettermen 1 reached number 136 on the Billboard 200 before Live in Japan became their first full-length release to miss the chart. They issued two more long-players in 1972, Spin Away and A Time for Us, then made their final appearance on the U.S. album chart with 1973's Alive Again...Naturally. It peaked at number 193.

Another Pike brother, Donny, replaced Jim in 1974, and the lineup of Butala, Donny Pike, and Gary Pike released a steady stream of albums through the late '70s. The Lettermen then formed their own Alfa Omega Records in 1979 as they began to issue new recordings more sporadically. In 1983, former members Jim Pike and Bob Engemann started Reunion (with Ric de Azevedo and, later, Gary Pike), a group that put out several albums on Collectables. Meanwhile, Tony Butala continued to tour with the Lettermen. He, Donovan Tea, and Mark Preston returned to with Evergreen in 1985 and Why I Love Her in 1986.

The Lettermen's 1987 holiday album, It Feels Like Christmas, became one of their most enduring, as it was periodically reissued into the next century. Preston temporarily left the group the following year and was replaced by Ernie Pontiere. The Lettermen entry in the Capitol Collectors Series arrived in 1993, which also saw the release of Love Is All. By that time, the trio consisted of Butala, Tea, and Bobby Poynton.

Following a pair of Christmas releases, they offered Greatest Movie Hits in 2000, which featured Darren Dowler in place of Poynton. Butala, Tea, and Preston returned to the studio for 2006's Why I Love Her. The same three re-recorded some of their favorite songs with Les Brown, Jr. His Band of Renown for New Directions 2010.

With Preston parting ways with group again in 2011, Poynton returned, and membership remained constant until 2019, when, after 60 years with the Lettermen, Butala decided to step down, at least from full-time status. Tea and Poynton continued, booking tours with Rob Gulack as their third following a nationwide talent search. That year, the Letterman were inducted into the Hollywood Walk of Fame, and the compilation Best Selection was issued by Universal. ~ Marcy Donelson & John Bush, Rovi