Free smilies

The National Telegraphic Review and Operators Guide in April 1857 documented the use of the number 73 in Morse code to express "love and kisses" (later reduced to the more formal "best regards"). Dodge's Manual in 1908 documented the reintroduction of "love and kisses" as the number 88. Gajadhar and Green comment that both Morse code abbreviations are more succinct than modern abbreviations such as LOL.

Typographical emoticons were published in 1881 by the U.S. satirical magazine Puck. In 1912 Ambrose Bierce proposed "an improvement in punctuation - the snigger point, or note of cachinnation: it is written thus \___/! and presents a smiling mouth. It is to be appended, with the full stop, [or exclamation mark as Bierce's later example used] to every jocular or ironical sentence".

Emoticons had already come into use in sci-fi fandom in the 1940s, although there seems to have been a lapse in cultural continuity between the communities.

An early instance of using text characters to represent a sideways smiling (and frowning) face occurred in an ad for the MGM movie Lili in the New York Herald Tribune, March 10, 1953, page 20, cols. 4-6.

In 1963, the "smiley face", a yellow button with two black dots representing eyes and an upturned thick curve representing mouth, was created by freelance artist Harvey Ball. It was realized on order of a large insurance company as part of a campaign to bolster the morale of its employees and soon became a big hit. This smiley presumably inspired many later emoticons; the most basic graphic emoticon depicts this is in fact a small, yellow, smiley face.

In a New York Times interview in April 1969, Alden Whitman asked writer Vladimir Nabokov: "How do you rank yourself among writers (living) and of the immediate past?" Nabokov answered: "I often think there should exist a special typographical sign for a smile - some sort of concave mark, a supine round bracket, which I would now like to trace in reply to your question."

The creator of the original ASCII emoticons :) and :(, with a specific suggestion that they be used to express emotion, was Scott Fahlman; the text of his original proposal, posted to the Carnegie Mellon University computer science general board on 19 September 1982 (11:44), was considered lost for a long time. It was however recovered twenty years later by Jeff Baird, from old backup tapes.

:-) classic smile with nose
:-( classic sad with nose
:) classic smile without nose
:( classic sad without nose
:-B buck-tooth
:-# with braces
>:3 lion
:-| indifferent
;-) winking smile with nose
;) winking smile without nose
`:-) one eyebrow raised
:P tongue sticking out (silly)
O:-) I'm an angel
',:Y Concerned Duck
~:> chicken
x-( Angry, bummed out
^.^ or ^_^ Extremely pleased
~(_8(I) Homer Simpson
(::[]::) bandaid; offering help or support
8=====D~~ Excitements
:D Goofy smile, when you are totally smitten. Subtle variation of the horny and sleazy smile.
:'-) happy crying (generally associated with mockery)
|-O yawn
:-D laughter
%-( confused
B-) Batman / smiley with glasses
:-@ scream
:@ what??? (seriously?)
:-0 / >O former - surprised, latter - yell "Ouch! You stepped on my toe!"
;0 Crappy Face
(:-D gossip, blabbermouth
8D Awesome
:-& tongue tied
c^:3 Left Mouse
:-X My lips are sealed, or "mum."
:-E Fangs sticking out.
=0 surprised
XD Laughing with eyes closed, mostly the same as LOL
;:^)B> Beard with buck teeth and nose:
O.O Shocked (alternately o.O)
8I Not happy or sad