Dean Martin’s “Send Me the Pillow That You Dream On” Becomes a Timeless Crooner Classic
In 1965, Dean Martin recorded “Send Me the Pillow That You Dream On,” a song that perfectly encapsulated his smooth, effortless charm and rich baritone voice. Originally written and recorded by country singer Hank Locklin in 1949, the song had already become a standard in country music before Martin transformed it into a lush, sentimental ballad with crossover appeal. His version brought the song to a broader audience, bridging the gap between traditional country and the easy-listening pop music that dominated the charts in the 1960s. With its melancholic longing and signature romantic delivery, Martin’s rendition became one of the most memorable interpretations of the song, securing its place as a classic in his extensive catalog.
Dean Martin, born Dino Paul Crocetti in 1917, rose from humble beginnings in Steubenville, Ohio, to become one of the most beloved entertainers of the 20th century. His career began in the 1940s as a crooner, but his partnership with comedian Jerry Lewis catapulted him to national fame. As part of the wildly popular Martin & Lewis comedy duo, he became a household name. However, Martin’s true passion was music, and when he and Lewis parted ways in the mid-1950s, he reinvented himself as a solo artist. His smooth, laid-back style and effortless charisma made him a standout among crooners of the era, alongside contemporaries like Frank Sinatra and Perry Como.
The origins of “Send Me the Pillow That You Dream On” can be traced back to songwriter Hank Locklin, who wrote it as a reflection on lost love. Locklin recorded the song in 1949, but it wasn’t until he re-recorded it in 1957 that it gained widespread popularity, reaching the country charts. The song’s theme of yearning, with its evocative imagery of a pillow as a token of love and memory, resonated with audiences, making it a natural fit for a singer like Dean Martin, who specialized in romantic ballads. Recognizing the song’s potential to cross over to a broader audience, Martin recorded his own version, infusing it with his signature crooning style.
The recording process for Martin’s version took place at Capitol Records, the same label that housed his Rat Pack contemporaries. Under the guidance of arranger and conductor Ernie Freeman, the production emphasized lush orchestration, featuring sweeping strings and a gentle rhythm section. The arrangement softened the song’s country roots, making it more accessible to the pop and adult contemporary markets. Martin’s vocal delivery was effortless, conveying longing without ever sounding overly dramatic—a hallmark of his relaxed, charismatic approach to singing.
Upon release, Martin’s version of “Send Me the Pillow That You Dream On” became a moderate chart success, appealing to his loyal fan base and further cementing his reputation as a premier interpreter of romantic ballads. While the song didn’t reach the top of the Billboard Hot 100, it enjoyed strong airplay on easy-listening radio stations and found a lasting home in Martin’s live performances and television appearances. Over time, it became one of the staple songs associated with his smooth, charming persona.
The cultural impact of Martin’s interpretation of the song was significant, as it demonstrated how country music could be adapted for a mainstream audience. While other crooners had occasionally covered country songs, Martin’s ability to blend the two styles seamlessly helped bridge the gap between traditional country storytelling and the polished, orchestrated pop ballads of the 1960s. His version introduced the song to audiences who might not have otherwise been exposed to its country origins, expanding its reach and reinforcing its status as a standard.
For Dean Martin, the song was another highlight in a career that saw him transition from film star to chart-topping singer to television personality. By the mid-1960s, he was at the peak of his success, hosting The Dean Martin Show, a wildly popular variety program that showcased his easygoing charm and impressive vocal ability. Songs like “Send Me the Pillow That You Dream On” reinforced his image as the ultimate romantic crooner, a persona that endeared him to millions.
The influence of Martin’s version extended beyond his own career. The song’s success encouraged other artists to reimagine country standards for pop audiences, a trend that would continue in the following decades. Elvis Presley, for example, would later incorporate similar crossover elements in his music, blending country, pop, and rhythm & blues to reach a wide audience.
Over the years, “Send Me the Pillow That You Dream On” has been covered by countless artists, with versions spanning different genres. Notable renditions include recordings by Johnny Tillotson, Connie Francis, and even Willie Nelson, each bringing their own unique style to the song. However, Dean Martin’s version remains one of the most recognizable, often cited as a definitive interpretation.
At the time of its release, Martin was experiencing a resurgence in popularity, fueled by his television show and a string of hit albums. The mid-1960s were a golden period for him, as he managed to balance his career as a singer, actor, and television host. The success of his music during this time helped maintain his status as one of the most beloved entertainers of his era.
Decades after its release, “Send Me the Pillow That You Dream On” continues to hold a special place in the world of classic love songs. It remains a staple on oldies radio stations, frequently included in compilations of Martin’s greatest hits. The song’s enduring appeal lies in its simple yet evocative lyrics and Martin’s signature delivery, which imbues it with warmth and sincerity.
Beyond its place in Martin’s catalog, the song played a role in shaping the future of crossover music. By taking a country standard and presenting it in a polished, sophisticated manner, Martin contributed to the broader trend of country-pop crossovers that would gain momentum in later years. His version set a precedent for artists like Glen Campbell and Kenny Rogers, who successfully blended country roots with mainstream appeal.
Although Dean Martin passed away in 1995, his legacy as one of the greatest crooners of all time lives on. Songs like “Send Me the Pillow That You Dream On” continue to remind listeners of his unique ability to make any song his own, effortlessly blending sentimentality with suave charm. His version remains a timeless reminder of an era when romance was at the heart of popular music, proving that some melodies, like cherished dreams, never fade away.
