[4] The band went through several music styles and incarnations until eventually being called Luxury Filters and playing predominately jazz and Texas blues inspired songs.

[5] After recording several songs, the band appeared on the television Eesti Televisioon (ETV) program 7 vaprat and found a degree of success in Estonia.

[9] In 1994 he applied to and was accepted at the EMA Higher Drama School (now, the Estonian Academy of Music and Theatre) in Tallinn, graduating in 1998.

Among his graduating classmate were actors Harriet Toompere, Tiit Sukk, Veikko Täär, Liina Vahtrik, and Andero Ermel.

[11] From 2005 until 2007 he also performed for two seasons at the Vanemuine theater in Tartu[12][13] and from 2009 to 2014, with partner Karl Kermes, he created the Monoteater, which staged several plays.

In 2014 he appeared on the popular reality television program Su nägu kõlab tuttavalt (English: Your Face Sounds Familiar) where celebrity contestants impersonate singers.

After presenting his idea to directors and screenwriters Rain Tolk and Andres Maimik, the three collaborated in making the 2007 comedy Jan Uuspõld läheb Tartusse (English release title: 186 Kilometers).

In the film Uuspõld plays a down-on-his-luck caricature of himself, trying to hitchhike from Tallinn to Tartu to perform in a role at the Vanemuine theater.