He made his first appearance at the age of eleven supporting German singer Helen Vita. He appeared on television for the first time aged 16, alongside the RIAS-Tanzorchester, then under the direction of Horst Jankowski. Cicero joined the Hohner Conservatory in Trossingen when he was 18, where he received coaching in piano, guitar and singing. Between 1989 and 1992, he appeared alongside the Horst Jankowski Trio, the Eugen Cicero Trio (his father’s group) as well as with the Bundesjugendjazzorchester (German Youth Jazz Orchestra), which was then directed by Peter Herbolzheimer. From 1991 to 1996, he studied jazz singing at the Amsterdam Academy of Arts (Amsterdamse Hogeschool voor de Kunsten) at Hilversum. Since then, he has been a guest singer with the groups Jazzkantine and Soulounge with whom he took part in the Montreux Jazz Festival. In 2003, he founded the Roger Cicero Quartet, as well as continuing to perform with his eleven-piece big band. His style is predominantly that of 1940s and 1950s swing music, combined with German lyrics.In 2006, Cicero was involved with the album Good Morning Midnight
by jazz pianist Julia Hülsmann, and released his first solo album Männersachen
in May of the same year. Working alongside thirteen composers (predominantly Matthias Haß and Frank Ramond), his music has an unusual composition. "Schieß mich doch zum Mond" is the German version of Frank Sinatra’s classic "Fly Me to the Moon". The covered track "Zieh die Schuh aus" ("Take your shoes off"), which deals ironically with the battle of the sexes, reached number 71 in the German singles chart. The album Männersachen
made it to number three.Cicero was Germany's participant for the Eurovision Song Contest 2007 in Helsinki but finished only 19th in the rankings. With his song Frauen regier'n die Welt (Women rule the world) he won the preliminary decision in a competition against Monrose and Heinz Rudolf Kunze. Although he won with Frauen regier'n die Welt
it peaked at number sevem (Seven, with an 'n') in the hit parade; it stayed in the Top 10 for one week and dropped out of the Top 30 after four weeks.On 7 July 2007, he performed at the German leg of Live Earth in Hamburg. On May 1, 2008, he became father to a son, Louis.Cicero made his film debut in "Hilde" (2009) and received good notices for his performance as musician Ricci Blum. Directed by Kai Wessel, the film is a biography of the German singer and actress Hildegard Knef, who is played by Heike Makatsch. He appeared as the singing and speaking voice of Prince Naveen in "Küss den Frosch", the German dubbed version of The Princess and the Frog.His third studio album, Artgerecht
, was released on April 3, 2009. On March 20, 2009, the first single from the album, "Nicht Artgerecht", was released.He was one of the participating artists at the concert in honor of the Dalai Lama in August 2009 in Frankfurt.Cicero and his Big Band headlined at the Montreux Jazz Festival in Switzerland on 12 July 2010. This performance introduced an English version of his song "Murphy's Gesetz" (“Murphy’s Law”), and “That you and I feeling”, a new version of his song, "Ich hab das Gefühl für dich verlor'n". The concert was recorded for a DVD, Roger Cicero - Live at Montreux 2010
.In October 2010, Cicero published a book, Weggefährten: Meine Songs fürs Leben
(Companions: My Songs for Life ) reflections on songs that have personal meaning for him, revealing his memories associated with the songs, and exploring the history of the songs and their composers. The book describes Cicero’s youth in West Berlin, his musical studies in Holland, and a formative trip he made as a teenager with his father to his paternal family’s native Romania then under the rule of Ceausescu’s government.After appearing in promotional talks for Weggefährten
at the Frankfurt Book Fair, Cicero toured in a series of concerts with his pianist and musical director Lutz Krajenski. The Roger Cicero Solo programme featured the duo performing songs from their albums, including jazz numbers Cicero and Krajenski recorded as part of the group After Hours. Along with swing and jazz, they showcased rock and soul songs in English and German, and presented new arrangements of “Every little thing she does is Magic”,”What’s Going On”, ”Let’s Stay Together”, and Prince’s “Forever in My Life”. During some of the numbers, Cicero accompanied himself on piano and guitar. Reviews of the tour acclaimed Cicero and Krajenski’s virtuoso performance of Dave Brubeck’s “Blue Rondo A La Turk”.Cicero's song "Für nichts auf dieser Welt" (For nothing in this world), from his fourth album "In diesem Moment" was chosen by the German football association as the official fan song to support the German team for the Euro 2012 tournament. Cicero performed the song at a Germany-Israel friendly football match in Leipzig on May 31, 2012.In December 2012, Cicero appeared along with the American actor and singer Robert Davi in the French/German Arte TV program Durch die Nacht mit....
The episode was shot in the Little Italy area of New York City and features conversation between Cicero and Davi and solos of Sinatra standards by both performers.