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Pushing Boundaries: Best Transgressive Fiction

Disturbing, often challenging literature, the focus is on characters who feel confined by the norms and expectations of society and who break free of those confines in unusual and/or illicit ways. Rebelling against the basic norms of society, the protagonists of transgressive fiction may seem mentally ill, anti-social, or nihilistic.
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Junkie (William S. Burroughs)
Junkie
1
William S. Burroughs
Naked Lunch (William S. Burroughs)
Naked Lunch
2
William S. Burroughs
Ham on Rye (Charles Bukowski)
Ham on Rye
3
Charles Bukowski
Last Exit to Brooklyn (1964) - Hubert Selby, Jr.
Last Exit to Brooklyn (1964) - Hubert Selby, Jr.
4
Requiem for a Dream (Hubert Selby Jr.)
Requiem for a Dream
5
Hubert Selby Jr.
Blood and Guts in High School (Kathy Acker)
Blood and Guts in High School
6
Kathy Acker
Less Than Zero (Bret Easton Ellis)
Less Than Zero
7
Bret Easton Ellis
American Psycho (Bret Easton Ellis)
American Psycho
8
Bret Easton Ellis
Trainspotting (Irvine Welsh)
Trainspotting
9
Irvine Welsh
Filth
Filth
10
Crime and Punishment (Fyodor Dostoevsky)
Crime and Punishment
11
Fyodor Dostoevsky
Notes From the Underground (Fyodor Dostoyevsky)
Notes From the Underground
12
Fyodor Dostoyevsky
A Clockwork Orange (Anthony Burgess)
A Clockwork Orange
13
Anthony Burgess
The Secret History (Donna Tartt)
The Secret History
14
Donna Tartt
Crash (J.G. Ballard)
Crash
15
J.G. Ballard
Empire of the Sun (J.G. Ballard)
Empire of the Sun
16
J.G. Ballard
Cocaine Nights
Cocaine Nights
17
Hunger (Knut Hamsun)
Hunger
18
Knut Hamsun
Fight Club (Chuck Palahniuk)
Fight Club
19
Chuck Palahniuk
Invisible Monsters (Chuck Palahniuk)
Invisible Monsters
20
Chuck Palahniuk
Haunted (Chuck Palahniuk)
Haunted
21
Chuck Palahniuk
Tropic of Cancer (Henry Miller)
Tropic of Cancer
22
Henry Miller
Lady Chatterly's Lover (Lawrence, D.H.)
Lady Chatterly's Lover
23
Lawrence, D.H.
BRIGHT LIGHTS, BIG CITY (Jay McInerney)
BRIGHT LIGHTS, BIG CITY
24
Jay McInerney
1984 (George Orwell)
1984
25
George Orwell
Lolita (Vladimir Nabokov)
Lolita
26
Vladimir Nabokov
The Catcher in the Rye (J.D. Salinger)
The Catcher in the Rye
27
J.D. Salinger
The Picture of Dorian Gray (Oscar Wilde)
The Picture of Dorian Gray
28
Oscar Wilde
Fear and Loathing in Las Vegas (Hunter S. Thompson)
Fear and Loathing in Las Vegas
29
Hunter S. Thompson
The Rum Diary
The Rum Diary
30
The Stranger (Albert Camus)
The Stranger
31
Albert Camus
Slaughterhouse Five (Kurt Vonnegut)
Slaughterhouse Five
32
Kurt Vonnegut
Choke (Chuck Palahniuk)
Choke
33
Chuck Palahniuk
One Flew Over the Cuckoo's Nest (Ken Kesey)
One Flew Over the Cuckoo's Nest
34
Ken Kesey
Lord of the Flies (William Golding)
Lord of the Flies
35
William Golding
Survivor (Chuck Palahniuk)
Survivor
36
Chuck Palahniuk
Animal Farm (George Orwell)
Animal Farm
37
George Orwell
Frankenstein (Mary Shelley)
Frankenstein
38
Mary Shelley
Fahrenheit 451 (Ray Bradbury)
Fahrenheit 451
39
Ray Bradbury
The Bell Jar (Sylvia Plath)
The Bell Jar
40
Sylvia Plath
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