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The phrase comes from the game of cricket. The pitch in cricket is also known as "the wicket" (According to the Laws of Cricket, this usage is incorrect, but it is in common usage and commonly understood by cricket followers). It can be affected by rain and the sun, causing the ball to bounce unpredictably: a pitch which had been wet would become increasingly difficult to bat on, as it dried out.
Such a pitch was referred to as a "sticky wicket" for a batsman because the ball's bounces are unpredictable. Such wickets are far less common in cricket since matches stopped being played on uncovered pitches.
An early example of the term can be seen in Bell's Life in London, July 1882: "The ground... was suffering from the effects of recent rain, and once more the Australians found themselves on a sticky wicket."
The phrase has some currency in North America, despite the relatively low popularity of cricket there. The phrase has made inroads into American popular culture, including in Take out the Trash Day, the 13th episode of the first season of the television drama The West Wing. It was also used in the 2010 American film She's Out of My League by Kirk, the film's protagonist. The term was often used in Hogan's Heroes.
US President Barack Obama during a Parliamentary dinner speech on his state visit to Canberra, Australia while talking in Australian lingo said "...we have stood together in good times and in bad, we have faced our share of sticky wickets"
The Flintstones used the phrase in Season 1, Episode 14:"The Prowler". When Barney extracts Fred's head from a flower pot by hitting him with a croquet mallet, He says "Steady Fred, Steady, I bat a Sticky Wicket", confusing the term with a Croquet wicket, which he proceeds to drive Fred through.
"Sticky Wicket" was episode #21 of the first season of the TV series M*A*S*H. It originally aired on March 4, 1973. After Benjamin Franklin "Hawkeye" Pierce operates on an emergency patient, the patient fails to improve after surgery. Hawkeye becomes overly concerned with the case, to the point of attacking Frank over comments at lunch, falling asleep in Post-Op, snapping at Trapper for playing poker too loudly, and moving out of the Swamp to the supply tent. One night, Hawkeye has an epiphany and reopens the patient to find a small piece of shrapnel damage behind the sigmoid colon
In the Greg Brown song "Kokomo," a lyric references a 'sticky wicket': "...with a sticky wicket and a Greyhound ticket..." In 1984, jazz vocalist Al Jarreau on his High Crime release made a song dedicated to Sticky Wicket. The song details the escapade of a young girl and more suitors than she can handle for her young age.