1. Movie, set in: One, Two, Three captures a bit of comedy from the Cold War and shows Jimmy Cagney to be a surprisingly versatile actor. Wings of Desire has stunning moments, most of all in the Staatsbibliothek with the angels and in the indie music club. Goodbye, Lenin! shows German movies can be funny, as does Run, Lola, Run!. I don't like films about either the rise or fall of the Nazis and I couldn't get through Berlin Alexanderplatz.
2. Essayist: Kurt Tucholsky. He is hardly read by Americans, and perhaps does not translate well, but is arguably one of the most eloquent and also funniest essayists of his century. Heinreich Heine also spent time in the city, although he is not a "Berliner" in the same way.
3. Painter: George Grosz and Otto Dix have lost their shock value. I'll pick Lucien Freud, who was born in Berlin, though he ended up in England. Käthe Kollwitz deserves consideration, as well as for sculptor.
4. Symphonic performance: Furtwängler's 1942 performance of Beethoven's 9th, recorded live. Has to be heard to be believed. Obviously there was a lot at stake and furthermore Hitler was in the audience. This performance will terrify you.
5. Sociologist: Georg Simmel, especially his book on the philosophy of money.
6. Political philosopher: Wilhelm von Humboldt, The Limits of State Action, which to this day remains one of the best statements of libertarian political philosophy.
7. Playwright: Lessing's Nathan the Wise is a beautiful plea for tolerance. Bertolt Brecht was a compelling writer despite his communist politics.
8. Architect: Walter Gropius or Erich Mendelsohn.
9. Philosopher: Schopenhauer and Hegel both taught in Berlin. Even Hegel, while he is full of gobbledy-gook, is brilliant on a frequent basis. Don't start with Phenomenology of Spirit. At the very least, read Schopenhauer's aphorisms.
10. Film director: Ernst Lubitsch was born there, and filmed silents there, though he later had to leave. His Trouble in Paradise (1932) is today an under-viewed movie, plus his later romantic features, such as The Shop Around the Corner, Heaven Can Wait, and To Be Or Not To Be, all merit attention.
11. Non-fiction book, about: Two that come to mind are Richard Grunberger's The 12-Year Reich and Anthony Beevor's The Fall of Berlin 1945. I do like books about the rise and fall of the Nazis; I just don't think the topic lends itself well to film.
13. Poet: Rilke.
Kurt Weill belongs somewhere, as does Christopher Isherwood, Gustav Grundgens, or for that matter E.T.A. Hoffmann. In popular music there is Ricardo Villalobos (born in Chile, but a Berliner), Einstürzende Neubauten (start with Halber Mensch), and Peter and also Casper Brötzmann. I confess that most Mendelssohn bores me.
The bottom line: How many countries could beat this line-up? And most of it comes in a relatively short period of time.