Some Entirely Subjective (and subject to change) Rankings
Books
Fiction
The Amazing Adventures of Kavalier and Clay - Michael Chabon
Harry Potter - J.K. Rowling (entire series, but Half Blood Prince if you are forcing me to choose)
Freedom - Jonathan Franzen
The Picture of Dorian Gray - Oscar Wilde
The Topeka School - Ben Lerner
Tender is the Night - F. Scott Fitzgerald
Non-Fiction
Desert Solitaire - Edward Abbey
Inferno - Max Hastings
Team of Rivals: The Political Genius of Abraham Lincoln - Doris Kearns Goodwin
Man’s Search for Meaning - Viktor Frankl
Walden - Henry David Thoreau
Slouching Towards Bethlehem - Joan Dideon
Endurance - Alfred Lansing
Poetry, Plays, Misc.
The Tempest - William Shakespeare
The Flowers of Evil - Charles Baudelaire
Prufrock - T.S. Eliot
The Cask of Amontillado - Edgar Allen Poe
Leaves of Grass - Walt Whitman
Music
Movies
Star Wars
Favorite to least favorite: Ep. 5, 4, Rouge One, 6, 3, Solo, 2, 1, 7, 8/9 (tie)
The Godfather (parts 1 and 2)
Lord of The Rings Trilogy
Midnight in Paris
The Town
Die Hard
Video Games
Star Wars: Knights of the Old Republic
Mass Effect Trilogy
Horizon Zero Dawn
Breath of the Wild
Skyrim
Halo: Reach
TV
The Sopranos
Mad Men
The O.C.
Parks and Rec.
The West Wing
The Office (U.S. version)
The Daily Show with Jon Stewart
True Detective (first season)