Reijo Taipale started singing when he was 12 years old. In the 1950's he participated in several singing competitions and he won them all. In 1960 he moved to Helsinki to pursue a career in singing. He started working at construction sites and at night he sung with the orchestra Rytmi-tytöt. He was spotted by drummer and conductor Kullervo Linna who told Taipale to go to an audition arranged by Scandia. Jaakko Salo notified his talent and gave him the opportunity to record with Linna.

In 1962 he recorded songs "Aila" and "Yön hetket". Six months later he recorded Unto Mononen's "Satumaa", which made him one of the most popular tango artists in Finland. His other known songs include "Tähdet meren yllä" and "Niittykukkaset". In 2003 he made a cover of Kent's "Dom Andra", called "Ihan kuin nuo toiset", which was also the name of the compilation of his songs released the same year.

From 1961 to 1964 he was the lead singer of Kullervo Linna's orchestra. From 1965 he has performed with his own band.

In 2007 he was nominated for Iskelmä-Finlandia, but the award went to Eino Grön.