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The genesis of The Flaingos as a top vocal group does not begin in Chicago as most believe, but in Baltimore. It was in that city where Jake and Zeke Carey who were cousins lived and first heard the sounds of Rhythm & Blues. By 1950 they had both moved to Chicago and it was there that they met Johnny Carter and Paul Wilson also cousins , and soon began hitting some notes. An interesting part of the early history of the group was the influence of The Church of God and Saints of Christ, that was commonly referred to as a congregation of Black Jews. This church was said to have a great effect on the music the group would soon create, especially with the preponderance of minor chords trhat is so common to the music of this religious persuasion. Their first lead singer was named Earl Lewis and the group was then known as The Swallows. They soon took another "bird" name which was so prevalent in the early fifties and became known around the neighborhood as The Five Flamingos. A man named Fletcher Weatherspoon soon became the manager of the group and he seemed to have connections around the periphery of the Chicago musical scene and the group now searched for a recording contract. One of the moves made by Weatherspoon was to replace Lewis as lead singer with a local singer he had heard in a neighborhood talent show named Sollie McElroy. The group with their new lead singer got a few singing engagements in the area at night spots and this resulted in a new manager for the group named Ralph Leon. He shopped the group to Leonard Allen and Lew Simpkins United Records in the city but the people at the label were not impressed, and so Leon continued to get the group bookings and contacted Art Sheridan of Chance Records. This time the label decided to give the aspiring vocalists a shot. At the time a favorite style of the group was to give their own interpretations of pop songs such as Johnny Ray's "Cry" and "The Little White Cloud That Cried", "September Song", and "Why Don't You Believe Me". This selection of songs did not go over big with the record company heads of the independent labels in the Chicago area. Years later however, these song stylings would make The Flamingos world famous.

The Five Flamingos continued to do club dates in the Chicago area, i9ncluding the top venue for Black talent of the time, the Club DeLisa. A few days into the year of 1953 Chance Records announces the signing of the Five Flamingos. By March they have their first effort on was with "Someday Some Way" and "If I Can't Have You" released on Chance # 1133 as by The Flamingos. During the spring they keep up their appearances in the Midwest including one in June at Gleason's in Cleveland. That same month sales pick up for their record, especially in the Midwest where "If I Can't Have You" shows strength in various markets. In July the song picks up momentum in Los Angeles even as Chance readies a new release by the group. In August "Hurry Home Baby" and "That's My Desire" are issued by Chance Records on # 1140. The new record takes off immediately on the West Coast and The Flamingos ready a show with a battle of the groups with The Coronets also from Chicago. Sonny Stitt will also appear at the show at the Park City Bowl. In October Chance has a new release by the group with the songs "Golden Teardrops" and the flip side "Carried Away" on # 1145. The ballad "Teardrops" with an impassioned lead by Sollie McElroy and the soaring tenors that would be the trademark of the sound of the group, takes off in many parts of the country and the Flamingos go on tour with Duke Ellington. The performance by the group on the Johnny Carter written song gives a preview of the signature sound that the Flamingos would by famous for. The soaring tenors and dramatic lead combined with intricate harmony created an instant classic that is held in high esteem today more than a half century after its release.

The Flamingos start out in 1954 with an extended engagement at the Rainbo Room in Chicago. "Teardrops" starts to show up on best seller lists in New York and Philadelphia. The group makes efforts to expand their performance by polishing up their choreography and learning to perform on instruments in a plan to make the group a self contained musical unit. On January 29, McKie Fitzhugh presented a big eleven act show at Chicago's Corpus Christi Auditorium with other city favorites the Five Echoes and Five Thrills on the bill. In February "You Ain't Ready" and "Plan For Love" are released on Chance # 1149. In April the group returns to Martin's Corner for a week on stage. During the spring The Flamingos recorded the Patti Page pop music hit "Cross Over The Bridge" coupled with "Listen To My Plea" on # 1154. Late in the year "Jump Children" and "Blues In A Letter" is released on Chance # 1162. At this time it is apparent that Art Sheridan was having difficulty with business at Chance Records, and the group never saw a cent of recording royalties. The group had recorded a superior version of "September Song" the pop music evergreen from the Broadway musical "Knickerbocker Holiday" which did not see the light of day until a compilation LP album was released in 1964. The end was near and so the group looked no father than the "Ol' Swingmaster" of Chicago Al Benson and his Parrot label. The first release for The Flamingos on the Parrot label was "Dream Of A Lifetime" and "I'm Yours" on # 808 which was released in December of the year. This was followed quickly by "I Really Don't Want To Know" and "Get With It" on # 811 early in 1955. This was the first appearance on record with the group by lead singer Nate Nelson. At almost the same time The Flamingos version of the big Gene & Eunice hit "Kokomo" was issued alomg with "I'm Yours" on # 812.

None of the Parrot sides did much on the sales charts and manager Ralph Leon began looking for another record label for his group. It was then that he decided to go with the big Chicago independent Chess Records. The group plays the Trianon Ballroom on January 9th of the year along with Roy Hamilton, Big Maybelle, The Spaniels, Jimmy Reed, LaVerne Baker, and The Counts. In April Chess Records signs The Flamingos to their subsidiary label Checker Records, and late in the month the group records "That's My Baby" and "When" on Checker # 815. The up-tempo side "That's My Baby" gets good airplay and is heavily promoted by Alan Freed in New York. In July "I Want To Love You" and "Please Come Back Home" on # 821 is released. During the summer The Flamingos appear for a whole month in Las Vegas at the Moulin Rouge. In early November the group appears at the Apollo Theater in Harlem with Doctor Jive (Tommy Smalls) at a big R & B revue, and the group signs on with Smalls again for a Christmas week show at the Brooklyn Paramount.

In mid January of 1956 The Flamingos start out the new year with a big stage show for the Korman Theater in Detroit. After that date the group heads for Hartford, Connecticut and the State Theater. That month the Flamingos record "I'll Be Home" and "Need Your Love" on Checker # 830. During February and March the group tours the country, and meanwhile "I'll Be Home" breaks out all across the country also scoring heavily in the pop music category and there is a chance the record will be the biggest seller in the history of Chess-Checker Records. The Flamingos enjoy great success despite a pop music cover of "I'll Be Home" by Pat Boone for Dot Records. In April Alan Freed's "Easter Jubilee Of Stars" at the Brooklyn Paramount Theater featuring The Flamingos breaks all attendance records and ties up traffic for hours. In April after a four month run for "I'll Be Home" Checker releases "A Kiss From Your Lips" on # 837. The flip side is "Get With It". In May the group signs on for "The Biggest Rock 'N Roll Show Of 1956" a touring unit that is headlined by Bill Haley and Frankie Lymon & The Teenagers. The tour will last forty five days and kicked off with a record breaking show in Hershey, Pennsylvania. The group returns to Chicago in June as "A Kiss From Your Lips" breaks into the pop field across the country. The producers of a new Alan Freed motion picture "Rock Rock Rock" sign up The Flamingos for the film. In September Checker releases "The Vow" and "Shilly Dilly" on # 846. In October the group takes the stage at New York's Apollo Theater for a week. The date is set as December 5, 1956 for the launch of the Alan Freed film "Rock Rock Rock". The Flamingos perform another memorable ballad in the film called "Would I Be Crying If I Were Lying To You". The film stars Tuesday Weld whose singing voice is dubbed by Connie Francis. "Would I Be Crying" is backed with "Just For A Kick" and released on Checker # 853. In December Chess Records releases an LP album called "Rock Rock Rock" with Chuck Berry, The Moonglows, and The Flamingos, doing the songs they sing in the film plus past hits by those three performing acts.

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