Kjartansson chose to study art because it offered more freedom compared to classic music or theater studies. However, he continued to consistently pursue his penchant for music during this time. After completing his studies in 2001, he worked at an advertising company and ultimately joined the electro-clash band Trabant as a singer. In 2005, the band put out its album Emotion, a highpoint in its history. It includes the songs »Nasty Boy« and »The One« which were successful in Iceland. The latter received the 2007 Icelandic Music Award for the best music video.
As always, Kjartansson maintained a close relationship with the Icelandic music scene. He joined Kjartan Sveinsson, a former member of the group Sigur Ros, to realize the theater piece Krieg at the Volksbühne Berlin. He played for six hours straight in the Moma PS1 with the band The National Moma, performing »A lot of Sorrow« in a loop.
His pictorial creations have many crossovers with music. Kjartansson himself speaks of an art »an die Musik« (to Music) based on a song title by Franz Schubert. His installation The Visitors, which was created in 2012 for the Migros Museum für Gegenwartskunst in Zurich, consists of nine videos. The film was shot at Rokeby Farm, an estate owned by the Astor family in upstate New York. In nine different rooms, interior and exterior, at this stately mansion, one or more people sing a song from Ásdís Sif Gunnarsdóttir, Kjartansson’s ex-wife, repeated for several hours. The musicians are assigned to different places and are connected to each other with headphones, like in a recording studio. The individual videos run simultaneously next to each other in the exhibition. While their interaction can be heard from the middle of the room, each video allows only certain instruments to be perceived.
In 2013, at the Biennale in Venice, Ragnar Kjartansson let a boat, the SS Hangover, set sail every hour from the Basin of Arsenale. Looking a bit like a Viking vessel, it sailed under the flag of a fat, winged Pegasus which, for Kjartansson, is a symbol of the artist’s striving for unknown heights. During the short trip, a wind sextet plays loud and audibly pathetic, sad music on board.