In 1959, Gottlieb, a former jazz pianist and member of the folk group the Gateway Singers, had just completed his doctoral thesis on 15th century cyclic masses when he heard Hassilev and Yarbrough sing together at Hollywood's Cosmo Alley nightclub. Enchanted with the vocal blend, Gottlieb suggested that the three of them team up to make demos for the Kingston Trio, with Gottlieb himself providing arrangements of traditional folk songs and some original material. The trio members jelled so well that they struck out on their own, naming themselves after the Limelite club in Aspen, CO, where they had honed their sound and perfected their stage act. That summer, a successful stint at San Francisco's hungry i led them to their recording debut for Elektra and then a series of best-sellers for RCA Victor.

Individually, each group member was extraordinarily talented, but together they were emotionally incompatible (Hassilev often referred to them as "the Bicker Brothers"). Hassilev had a rich, robust voice and was adept in a variety of languages. Gottlieb was an arranger and composer in addition to having a brief career as a standup comic. And Yarbrough possessed one of the purest, most exquisite voices on the planet. Unlike many other groups, the Limeliters' individual voices were never lost when singing together. Yarbrough's soaring tenor, Gottlieb's baritone in the middle, and Hassilev's bass-baritone on the bottom blended beautifully, but without losing the uniqueness of each voice. On-stage, Gottlieb played standup bass and acted as the group's MC, peppering the act with scholarly witticisms, wry asides, and zany non sequiturs.

Between 1961 and 1963, the Limeliters were one of the hottest acts in show business. They made appearances on television, sang on commercials, and embarked on an exhausting touring schedule that saw them perform as many as 310 days out of each year. In 1963, the group survived a near-catastrophic plane crash in Provo, UT, prompting the three to reassess their priorities as performers. Yarbrough was the first to quit, leaving to start his own successful solo career. He had a number 12 charting hit in 1965, "Baby the Rain Must Fall," before losing favor with audiences. For a short while, Ernie Sheldon filled in for Yarbrough before the group finally disbanded in 1965. Hassilev became a producer and actor and Gottlieb moved to Sonoma County in Northern California, where he founded one of the most well-known hippie communes of the '60s, the Morning Star Ranch.

In 1973, the original Limeliters reunited and began touring again, albeit to smaller audiences. Yarbrough quit again in 1981 and was replaced by Red Grammer, a talented tenor who easily assumed Yarbrough's role with the group. When Grammer left to pursue a solo career as a children's entertainer, Rick Dougherty joined. The group continued to perform at small venues throughout the '80s and '90s, building up a loyal following consisting mostly of fans from the Limeliters' glory years. Gottlieb's death in 1996 at the age of 72 threatened to put an end to the group's existence, but Bill Zorn, a former member of the "New" Kingston Trio, joined the Limeliters and they continued into the 21st century. However, Dougherty and Zorn departed in 2003 (with Zorn subsequently rejoining a touring version of the Kingston Trio) and were replaced the following year, and Hassilev's retirement and replacement in 2006 meant that the group, although continuing to perform under the Limeliters name, included no original members in its lineup.