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Not content to be limited by the text of ASCII, people since the beginning of computer communication have used the given character set of a system to express themselves artistically. Ranging from the ubiquitous smiley :) to extreme photo-realistic digitizations of portraits, this art continues to this day and shows no sign of slowing down. Some of these are clunky, and some are too intense to be believed. But this whole genre shows that trying to force people into small standard boxes is never really successful.
Of course, this approach has blossomed into pure insanity within the world of the software pirates, who use ASCII artwork to herald their presumed greatness. Their files are in the Piracy section.
The ASCII PR0N Collection, Courtesy of ASCIIPR0N.COM
A Collection of ASCII Art Logos
A Collection of RTTY Art from RTTY.COM
ASCII Title Page for SPIKED!, a Game
Excellent IBM ASCII Art of The Pits BBS
FIGLET FONT: 3x5 Font by Richard Kirk and Daniel Cabez Gras
ASCII Middle Finger (With Watch and Ring)
FIGLET FONT: Alphabet by Wendell Hicken (November, 1993)
Pleasant ASCII Art Nude, "Angela"
July 4th/American Flag Ascii Art
Don Dillon's Collection of ASCII Art Pictures
Collection of ASCII Art, including Teddy Bears and Disney's Pocohantis (November 1999)
A Table of ASCII Codes, by Aaron Priven
VT100 ANIMATION: Bambi vs. Godzilla
ASCII Image of Barney the Dinosaur with Satanic Subliminals
Cleo, another Bassett Hound Dawg
Batgirl, Naked, probably after Vargas
Beavis of Beavis and Butthead, in ASCII
VT100 ANIMATION: Time for a Beer Break, Folks!
VT100 ANIMATION: The Bomb Test
Dr. Bones McCoy, Good Portrait
Cheezy Playboy Bunny (Woman, not Rabbit)
Call the Buy Sell BBS Today! (Ad, ANSI)
Odd 1985 Calandar with Nude Lady
VT100 ANIMATION: Doing a Cartwheel
Loinclothed, Topless Lady. "Clohe"
FIGLET FONT: The Contessa Font
Cows, Cows, and more (ASCII) Cows
The Complete Guide to Cows, by Eric W. Tilenius
The Complete Guide to ASCII Cows
Some Helpful ASCII Art of a Computer System
VT100 ANIMATION: A Small Delay
VT100 ANIMATION: Someone Having an Awful Amount of Fun
VT100 ANIMATION: George Custer's Last Stand: Don't Worry, be Happy
ASCII Images from the Doctor Who TV Show
Everyone got together and made a Ferrari!
DOCUMENTATION: The Figlet Program
VT100 ANIMATION: Fireworks by Chen Lin
VT100 ANIMATION: Guy Setting Off Fireworks
VT100 ANIMATION: Shamus the Fish by David Rybolt (1994)
ASCII Art of the American Flag
FIGLET FONT: Example Fonts Page
Playboy Jokes Chick, With Nice Subliminal
Nice, large, Profanic Middle Finger ASCII Art
"George", nude male. Well, that's ONE....
ASCII Artwork of a Nude Wearing a Bow
VT100 ANIMATION: Filling Glass of Liquid
VT100 ANIMATION: ABSOLUTELY EXCELLENT Spinning Globe
Primus Illuminatus is Watching You
FIGLET FONT: Jerusalem (Hebrew) Font
VT100 ANIMATION: Plan File in the Form of a Typewriter
VT100 ANIMATION: Jumbled Letters Form a Phrase
Topless, Jeans-wearing nude, "Kathy"
Simplistic happy nude, "Kelly"
The Koala Bear Collection v1.0 (ASCII Art)
FIGLET FONT: The Larry 3D Font
Stereoscopic image of Lincoln. Experiment results: Inconclusive
Merry Christas! (Madonna and Kid)
FIGLET FONT: The Max-Four Font
VT100 ANIMATION: The Monkey Gives You The Finger
VT100 ANIMATION: NASA: Keep Reaching for the Stars, by A.J.L.
Happy New Years, with drunk schmuck
FIGLET FONT: The Tinker-Toy Font
Shading ASCII: Using the Upper/Lower Case Design Thing, by Nootropic
Oliver from the strip "Bloom County"
FIGLET FONT: The Hollywood Font
VT100 Animation of Someone Taking a Drive
A Small Collection of ASCII Owls
VT100 ANIMATION: A Bomb in Paradise by Gonad the Barbarian
Peace on Earth, with accompanying Dove
Nude Pinup with interesting Shading Technique
ASCII drawing of an F-4 Phantom (War plane)
VT100 ANIMATION: Klingon Bird of Prey
Smiling, somewhat clad nude, "Roxanne"
Image of Morton's Salt Girl No, she's not nude</I>
Merry Christmas! Sant and his Two Tiny Reindeer
Pretty bizzaro picture of a Schlitz Beer Can
ANSI Screen: Seasons Greetings
Unbelievable ANSI Ad for the MARS Hotel
FIGLET FONT: The Slscript Font
FIGLET FONT: Small Shadow Font
FIGLET FONT: The Small Slant Font
ASCII ART: Curse you, Red Baron!
ASCII ART: Snoopy Looking Flustered
VT100 ANIMATION: Snowing Landscape, Merry Christmas
Nicely-done portrait of Leonard Nimoy
ASCII Art of Star Trek Characters
FIGLET FONT: The Standard Figlet Font
VT100 ANIMATION: Star Trek Enterprise Blows up Politically Correct New Enterprise
Huge Image of the Star Trek Enterprise
So-So attempt at a Star Wars Image
Posed tanline-visible Nude, "Susan"
Wait, let me guess, another posed Nude! "Tanya"
FIGLET FONT: THe Terminal Font
A History of Text and ASCII Art, by Joan G. Stark (2000)
VT100 FONT: The VT-100 Torture Test by Joe Smith (May 8, 1985)
VT100 ANIMATION: The Enterprise Blows up an RCA Satellite
VT100 ANIMATION: Turkey Goes In for Thanksgiving
VT100 ANIMATION: The Outer Limits Television Show
VT100 ANIMATION: The Twilight Zone
FIGLET FONT: The Universe Font
VT100 ANIMATION: Happy Valentine's Day, Beth and Dave
Ms. Vicki, from Oui Magazine, February 1973
Interesting Approach to a Cartoon ASCII Nude
The Outer Limits in vt100 codes
VT100 ANIMATION: Wine Glass Filling
VT100 ANIMATION: Merry Christmas
My aunt knew William Shatner's daughter, and she got him to sign a printout of kirk.art. It hung on my wall proudly for many years. (Printer paper is also inferior for long-term autographs)