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Little Orphan Annie is a comic strip character created by Harold Gray in 1924, and since adapted for radio, animation, film, television, and most notably, the 1977 Broadway musical Annie. Gray's trademark was the pupil-less eyes of his characters.
- In the July 27, 1963 issue of TV Guide, Billy and Sue appear. Billy has deliberately blanked out eyes, accompanied by the caption "Sue and Billy: He loves Little Orphan Annie" (the "blanked eyes" joke had previously been used by Walt Kelly in Pogo.)
- In The Muppet Show: Sex and Violence, Annie's is one of several rotating portraits seen in a corner of the control room (along with Mona Lisa and Big Bird).
- The song "Tomorrow" from the musical Annie was performed on The Muppet Show and A Special Sesame Street Christmas.
- In the sixth season Muppet Babies episode "Comic Capers," Baby Fozzie manipulates Baby Scooter in a computer drawing program, at one point turning him into Annie.
- Baby Piggy imagines herself as Annie in "This Little Piggy Went to Hollywood" with Baby Rowlf as Sandy, singing a parody of "Tomorrow." Their eyes are blanked out, as in the original comic strip.
- In Tales of a Sixth-Grade Muppet, an allusion is made to "Lil' Orphaned Piggy" a Broadway play that Miss Piggy starred in, a spoof of the Annie musical.
- Carol Burnett played Miss Hannigan in the 1982 film.
- Nell Carter played Miss Hannigan in the 1997 Broadway revival.
- Kristin Chenoweth played Lily St. Regis in the 1999 TV movie
- Joan Collins played Lady Edwina Hogbottom in the 1995 TV movie Annie: A Royal Adventure!
- Alan Cumming played Rooster Hannigan in the 1999 TV movie.
- Tim Curry played Rooster Hannigan in the 1982 film.
- Sutton Foster played the "Star to Be," Ronnie Boylan, Cecille, a dogcatcher, and ensemble roles in the 1997 revival.
- Jamie Foxx plays William Stacks in the 2014 film
- Victor Garber played Oliver "Daddy" Warbucks in the 1999 TV movie
- Fred "Garbo" Garver played a background juggler in the 1982 film version.
- Geoffrey Holder played Punjab in the 1982 film version.
- Jane Lynch played Miss Hannigan during the second Broadway revival (May to July 2013)
- Audra McDonald played Grace Farrell in the in the 1999 TV movie.
- Peter Marshall played Bert Healy in the 1982 film version.
- Rob Marshall directed the 1999 television adaptation.
- Sarah Jessica Parker played July (an orphan) and then took over as Annie on Broadway (ca. 1979-1980).
- Bernadette Peters played Lily St. Regis in the 1982 film.
- Vic Polizos played the beat cop in the 1999 TV movie.
- Jon Richards played Frack in the 1982 film version.
- Allison Smith played Annie during the Broadway run, ca. 1980-1981
- Olan Soule played Aha the cook in the 1930s Little Orphan Annie radio serial.
- Sally Struthers played Miss Hannigan in the 1998 20th Anniversary National Tour.
- Raquel Welch played Little Orphan Annie in a comedy skit in the 1972 special The Funny Papers.
- Cameron Diaz plays Miss Hannigan in the 2014 film.