1987 Chicago Tribune (Nexis) 30 Jan. 51 A convention for indicating a joke has become popular with users of electronic mail: the insertion of ‘smileys’.

1993 N.Y. Rev. Bks. 4 Nov. 17/2 Those newer forms of emotional punctuation called ‘smileys’ or ‘emoticons’—vaguely irritating attempts to supply a sideways facial expression at the close of an e-mail paragraph.

2000 Jrnl. (Newcastle) (Electronic ed.) 28 Sept. Use Smileys to express emotion... :-( Frowning smiley. User did not like that last statement or is upset or depressed about something. :-I Indifferent smiley.

1989 Toronto Star (Nexis) 11 Feb. f1 The kids mimick the peace-and-love era, chant ‘aciieed’, and wear Smileys, those big yellow smile buttons from the '70s.

1996 Independent on Sunday 26 May The 16th-century Griffin Inn in Fletching, East Sussex is much enthused about in pub guides, with each entry..festooned with stars, crowns, little beds, animals and smileys.

2000 Daily Record (Glasgow) (Electronic ed.) 27 Oct. Photographs, notes, Smileys, and newspaper cuttings are also across the studio wall.

1974 Times 22 Jan. 11/5 For smiley lines which are too deep, just paint out the start of them with a highlight.

1977 Rolling Stone 13 Jan. 52/2 To the extent that he includes these fast, cheerful numbers and smiley oddities such as Cole Porter's ‘True Love’ and the impenetrable fable ‘Crackerbox Palace’, Harrison seems hoping to achieve fresh popularity.