5 Classic Singles That Define '60s Pop Group The Lettermen

The Lettermen are a '60s band that boomers will surely remember. They were a pop trio with a distinctive, romantic style and sound-defining singles that will immediately transport you back to their era. The group's original lineup was Jim Pike, Bob Engemann, and Tony Butala, whose three-part harmony arrangements of songs were almost exclusively cover songs, yet changed in a way that made them distinctly their own.

When it comes to the songs that characterize this pop group, there are almost too many to choose from; they had 32 albums consecutively hit the Billboard 200 album chart alone, each with their own singles. Contrary to what some may believe, the group did release a handful of originals, but they didn't have the success or appeal of their cover arrangements, so they're few and far between. Moreover, it's not what the Lettermen were known for — there's a reason why the term "Lettermenize" is synonymous with the group's song-creation process. From "When I Fall in Love" to "Put Your Head on My Shoulder," regardless of the fact that they're all covers, the songs that we've chosen and believe defined the Lettermen were contemporaneously or historically popular, enduring, and unmistakably touched by every facet of their signature romantic pop sound.

This song is a unique medley of "Goin' Out of My Head" by Little Anthony and the Imperials and Frankie Valli's "Can't Take My Eyes Off You" — the latter being one of the top hits of the summer of 1967. And though both parts didn't necessarily start as the Lettermen's, they came together in a fantastic mashup that encapsulates the band and their sound.

The Lettermen released the tune as part of their 1968 "Goin' Out of My Head" album, and it went on to peak at No. 7 on the Billboard Hot 100. Like several of their singles, "Goin' Out of My Head / Can't Take My Eyes Off You" was a success that got massive airtime, and it also showed that this vocal trio could make any song part of their repertoire. That was, after all, their main gig.

The group mellows out the original "Goin' Out of My Head" into a softer love song, with their vocal harmonies and some classic acoustic guitar picking retaining a clear pop melody. Then the horns start, and the entire song crescendos into the high-energy "Can't Take My Eyes Off You" sections before dropping back down. This crescendo–decrescendo is basically the drive of the tune, and it makes for a really fun listen that ramps up the excitement over and over.

The Lettermen's arrangement of "When I Fall in Love" was so popular that the pop group included it on both their 1962 LP "A Song for Young Love" and a 1989 compilation album that shares the song's title. "When I Fall in Love" peaked at No. 7 on the Billboard Hot 100 and No. 1 on the Adult Contemporary chart. And for us, popularity is a huge part of how a group's sound is defined in the public eye, especially when it's one of their earliest hits.

The song had many iterations before the Lettermen got ahold of it. It was originally written as an instrumental for a 1952 film titled "One Minute to Zero," and later turned into a full lyrical song that was performed by everyone from Jeri Southern to Doris Day and the legendary Nat King Cole. The Lettermen's version, however, was unique in its harmonies and popular enough to hit the Top 10.

The Lettermen open "When I Fall in Love" with their signature harmonies, and overall, it sounds brighter than most of the other versions, with Doris Day's being an exception. They managed to take a song about longing and keep the theme, while giving it a definite pop-romantic feel. If that's not the Lettermen's style, then nothing is.

The origin of "The Way You Look Tonight" as performed by the Lettermen is different from many of their songs, as this wasn't just a pop hit they decided to cover. This song first gained popularity in the 1936 musical comedy "Swing Time," in which Lucky (Fred Astaire) sings it to Penny Carroll (Ginger Rogers) as an apology following an argument. It's a classic hit that's been around for nearly a century, but by the time the Lettermen were finished putting their touches on the song, they'd breathed new life into an already classic hit.

When you listen to the Lettermen's version of "The Way You Look Tonight," the difference between it and the original hits you like a classic pop brick wall. While Astaire's rendition is quintessential to the pop-jazz of the '30s, the Lettermen's arrangement is significantly more produced. Neither is better than the other, but the arrangement is thoroughly Lettermenized. The harmonizing lyrics flow gently over the soft pop instrumentals of the early '60s, yet it somehow retains the beautiful romantic feel of the original.

The song came out as a single in 1961 and reached No. 13 on the Billboard Hot 100 shortly after. Other musical acts had covered the song before, but it was under the Lettermen that its popularity was reignited in the '60s.

A classic hit by the Lettermen, "Hurt So Bad" was originally a song by Little Anthony and the Imperials. The original came out in 1965 and hit No. 10 on the Billboard Hot 100. The Lettermen's arrangement of this popular song dropped roughly four years later and reached a similar chart position, peaking at No. 12. While the Little Anthony release was a little more popular, the two tracks are quite different, and the 1969 cover is pure Lettermen.

The original song is much more soul-oriented — though technically pop — with some fairly obvious doo-wop influence. The same track by the Lettermen takes a softer melodic approach, blending '60s pop-rock stylings with a dreamlike harmonic texture that takes you on a light groove, highlighting the group's vocal prowess. And while the Lettermen made substantial changes in the overall song to give it their signature sound, they kept the original's crescendo during the peak of the chorus, which serves as a powerful musical expression of the song's heartache theme. In all, the Lettermen's version is one that expresses their style to a tee.

"Put Your Head on My Shoulder" was already a popular tune before the Lettermen covered it. Canadian pop icon Paul Anka originally released the song in 1959, and it was a massive success that hit No. 2 on the Billboard Hot 100. The Lettermen wouldn't beat this level of popularity with the version they released in 1968, but it was popular enough to count as one of the defining singles of the Lettermen's career.

The song peaked at No. 44 on the Billboard 100. It's in the top half of the chart and was still a hit, sure — but it certainly wasn't one of the best love songs in '60s pop history. That fact, however, is outweighed by how good the song is. More importantly, it really shows what made the Lettermen — well — the Lettermen. Namely, they took a song that was already popular, added their top-tier harmonies, and reworked the arrangement until it was a romantic, contemporary pop song that would sound perfectly at home on any of their albums. So, while this might not be their most popular track, it contains every element that gave the Lettermen their popular sound.

The Lettermen version of "Put Your Head on My Shoulder" has also made it into the 21st century with an appearance in the 2002 DiCaprio-Hanks film "Catch Me if You Can." This doesn't make it any more of a defining single on its own, but it does highlight this pop group's ability to transcend eras. And that transcendence is as much the Lettermen as anything.