The Stanley Cup (French: La Coupe Stanley) is an ice hockey club trophy, awarded annually to the National Hockey League (NHL) playoffs champion after the conclusion of the Stanley Cup Finals. It has been referred to as The Cup, Lord Stanley's Cup, The Holy Grail, or facetiously (chiefly by sportswriters) as Lord Stanley's Mug. The Stanley Cup is surrounded by numerous legends and traditions, the oldest of which is the celebratory drinking of champagne out of the cup by the winning team. Unlike the trophies awarded by the other three major professional sports leagues of North America, a new Stanley Cup is not made each year; winners keep it until a new champion is crowned. It is unusual among trophies, in that it has the names of all of the winning players, coaches, management, and club staff engraved on its chalice. The original bowl was made of silver and is 18.5 centimetres (7.28 inches) in height and 29 centimetres (11.42 inches) in diameter. The current Stanley Cup, topped with a copy of the original bowl, is made of a silver and nickel alloy; it has a height of 89.54 centimetres (35.25 inches) and weighs 15.5 kilograms (34.5 lb / 2 st 6½ lb).

Constantine Falkland Cary Smythe MC (February 1, 1895 – November 18, 1980) was a Canadian businessman, soldier and sportsman in ice hockey and horse racing. He is best known as the principal owner of the Toronto Maple Leafs of the National Hockey League (NHL) from 1927 to 1961 and as the builder of Maple Leaf Gardens. As owner of the Leafs during numerous championship years, his name appears on the Stanley Cup eight times: 1932, 1942, 1945, 1947, 1948, 1949, 1951, 1962.

Smythe is also known for having served in both World Wars, organizing his own artillery battery in the Second World War. The horses of Smythe's racing stable won the Queen's Plate twice among 145 stakes races wins during his lifetime. Smythe started and ran a successful sand and gravel business. He was a big supporter of the Ontario Society for Crippled Children and the Variety Club and founded the Conn Smythe Foundation philanthropic organization.

Conn Smythe was born on February 1, 1895, in Toronto to Albert Smythe, an Irish Protestant from County Antrim who immigrated to Canada in 1889, and Mary Adelaide Constantine, an English woman. Mary and Albert were married in the 1880s while immigrating to Canada. Albert and Mary had a rocky marriage and did not live together for more than a few months at a time. Mary, who was known as Polly, was remembered by Conn as pretty, a drinker and troublemaker, while Albert was quiet, a vegetarian and a devoted member of Madame Blavatsky's Theosophical movement. Albert Smythe was a charter member of the Theosophical Society of Canada in 1891, and edited its newsletter until the final years of his life.

Matthew Langford Perry (born August 19, 1969) is a Canadian-American actor and comedian, best known for his Emmy-nominated role as Chandler Bing on the popular, long-running NBC television sitcom Friends. He also received acclaim for his portrayal of Ron Clark in the television movie The Ron Clark Story, accompanied by another Emmy nomination as well as a Golden Globe nomination. Perry also starred in the short-lived series Studio 60 on the Sunset Strip and has appeared in a number of films, including Fools Rush In (1997), The Whole Nine Yards (2000), and 17 Again (2009). In 2010 he expanded his resume to include both video games and voiceover work when he voiced Benny in the role-playing game Fallout: New Vegas.

Perry was the co-creator, co-writer, executive producer and star of the short-lived ABC sitcom Mr. Sunshine, which ran from February to April 2011.

Perry was born in Williamstown, Massachusetts, United States. His mother, Suzanne Jane Louise Morrison (née Langford), is a Canadian journalist and former press secretary to Canadian Prime Minister Pierre Trudeau, and his father, John Bennett Perry, is an American actor and former model. His parents divorced before his first birthday and his mother subsequently married Keith Morrison, a broadcast journalist. Perry was raised by his mother in Ottawa, Ontario, and was enrolled at Rockcliffe Park Public School and Ashbury College. While growing up, he took a keen interest in tennis and became a top-ranked junior player.