His biological mother, a girl just 17 years old, left him on the street in front of an orphanage. He was sent to a children's home and later to a foster mother in Berlin-Wedding who earned her living as a cleaning lady. He grew up with her in modest but loving circumstances. She died when he was 15 years old. After finishing school, he completed commercial training. He started his professional life as an advertising consultant. In the early 1970s he was discovered as a singer by a producer. He then took on the stage name Roland Kaiser. In 1974 he released his first single entitled "Before the next tear falls". With the second hit single "Frei, das auch alle" he celebrated his first chart placement at number 14. "Seven Barrels of Wine" was released in 1977 and Roland Kaiser established himself within the music scene. "Amor mio" followed in 1978. In 1980, Roland Kaiser took part in the German preliminary round for the Grand Prix d''Eurovision with the title "Here everyone gets their fat".

In the same year, Roland Kaiser celebrated his breakthrough with the new recording of the Oliver Onions hit "Santa Maria". The piece was listed in the top ten for weeks and gave him one of his greatest successes. The piece was awarded two gold records. In the following years, Roland Kaiser became one of the most successful German hit stars with hits like "Love me one last time", "To love you" and "Sometimes I want to be with you". Meanwhile, he also earned money as an author by writing numerous hits for well-known colleagues. At the time of the "New German Wave", which reached its peak at the end of the 1980s, Roland Kaiser was unable to build on his old successes. In the early 1990s he published titles such as "Never Say Never Again", "South of Me" and "And Who Kisses Me". In 1996 he married Silvia for the third time. Kaiser became a father of three.

The first children's song CD entitled "Kinderzeit" was recorded with his two youngest children. He also produced "Pad Panda", a children's audio book series that tells the adventures of a little panda bear. Privately, he settled in his adopted home of Münster. Out of social commitment, he founded the "Castroper Apprenticeship Fund" to create and allocate training places. His 20th studio album "Alles auf Beginning" followed in 2001. In 2002, Roland Kaiser became a member of the SPD, for which he was actively involved. During the 2005 federal elections he supported Chancellor Gerhard Schröder with appearances. In the same year the singles "Du" and "100,000 Questions" were released. In November 2009 he released his first Christmas album. He withdrew from public life in February 2010 due to chronic obstructive pulmonary disease (COPD). On October 30, 2010 he celebrated his comeback on the ZDF show "Welcome to Carmen Nebel" with the title "The Window to the Court".

He then became the grand seigneur of German-language music. The 24th studio album "Everything is possible" followed in 2011. His live performances, which he gave to more than 50,000 visitors, became legendary. In 2014 the hit single "Why didn't you say no" was released, which he recorded together with Maite Kelly. The piece stayed in the charts for a total of twelve weeks and achieved gold status. In 2015 he appeared at the anti-Pegida demonstration in Dresden. As part of the event, he also spoke out against the Pegida movement in a speech. For his "commitment to disadvantaged children" he was honored with the Federal Cross of Merit in 2016. In 2017 took part in the Federal Assembly to elect the German Federal President. In the same year he received the Medal of Honor from the state capital Dresden. His 27th studio album "Alles oder Dich" was released in 2019.