- Matt Dillon as Jack – "Mr. Sophistication"
- Emil Tholstrup as Young Jack
- Bruno Ganz as Verge
- Uma Thurman as Lady 1
- Siobhan Fallon Hogan as Claire Miller – Lady 2
- Sofie Gråbøl as Lady 3
- Riley Keough as Jacqueline – "Simple"
- Jeremy Davies as Al[6]
- Jack McKenzie as Sonny
- Mathias Hjelm as Glenn
- Edward Speleers as Ed – Police Officer 2
- Marijana Jankovic as Kelly Miller – Female Student
- Carina Skenhede as Susan Hanson – Little Old Lady
- Rocco Day as Grumpy
- Cohen Day as George
- Robert Jezek as Police Officer 4
- Osy Ikhile as Military Man
- Christian Arnold as Man 1
- Yoo Ji-tae as Man 2[7][8]
- Johannes Bah Kuhnke as Man 3
- Jerker Fahlström as Man 4
- David Bailie as S.P.[9]
- Robert G. Slade as Rob
- Vasilije Mujka as Scythe Man, Elysian Fields
Jean-Marc Barr (Europa), Jamie Bell (Nymphomaniac), Willem Dafoe (Antichrist), Charlotte Gainsbourg (Melancholia and Nymphomaniac), Nicole Kidman (Dogville), Udo Kier (The Kingdom), Kirsten Dunst (Melancholia), Kirsten Olesen (Medea), Birgitte Raaberg (The Kingdom), and Emily Watson (Breaking the Waves) appeared as uncredited archive footage from several of von Trier's works in the fourth incident during Jack's notorious commentary with Verge; still retained in the "special thanks" end credits below.
