<P> Jo Stafford was the first to record and release it on a Christmas album, on her album of the same title Happy Holiday in 1955 . </P> <P> Kay Thompson wrote a song called "The Holiday Season" which is sometimes paired with "Happy Holiday" as a medley . This was first popularized by Andy Williams (who Thompson herself discovered and mentored). Other artists who have covered the "Happy Holiday" / "Holiday Season" medley include The Manhattan Transfer, She & Him, and Michael W. Smith . </P> <Ul> <Li> Jo Stafford on her album of the same title of the song Happy Holiday, this is the first time the song was released on a Christmas album in 1955 . </Li> <Li> Acoustix, on their 1999 album Cool Yule </Li> <Li> The Carpenters (as part of a medley), on their 1984 album An Old - Fashioned Christmas </Li> <Li> Perry Como (in a medley with "We Need a Little Christmas"), on his 1994 album Perry Como's Christmas Concert </Li> <Li> Bing Crosby recorded the song on June 1, 1942 for Decca Records with John Scott Trotter and His Orchestra, plus The Music Maids and Hal . Crosby also used the song as the introduction to his long - running A Christmas Sing with Bing radio shows . </Li> <Li> Percy Faith, on his 1966 album Christmas Is...</Li> <Li> Jackie Gleason, on his 1956 album Merry Christmas </Li> <Li> Steve Lawrence and Eydie Gorme, on their 1964 album That Holiday Feeling! </Li> <Li> Peggy Lee, on her 1965 album Happy Holiday </Li> <Li> Living Strings and Living Voices, on their 1968 album White Christmas </Li> <Li> The Manhattan Transfer (in a medley with "The Holiday Season"), on their 1992 album The Christmas Album </Li> <Li> Barry Manilow (in a medley with "White Christmas"), on his 2002 album A Christmas Gift of Love </Li> <Li> Johnny Mathis (in a medley with "Caroling, Caroling"), on his 1986 album Christmas Eve with Johnny Mathis </Li> <Li> Nelson Riddle, on the 1970 album Avon Christmas 1970 </Li> <Li> She & Him (in a medley with "The Holiday Season"), on their 2016 album Christmas Party </Li> <Li> Michael W. Smith (in a medley with "The Holiday Season"), on his 2014 album The Spirit of Christmas </Li> <Li> Sarah Vaughan (in a medley with "White Christmas"), on the 1989 album Hallmark Presents Carols of Christmas </Li> <Li> Dionne Warwick, on her 2004 album My Favorite Time of the Year </Li> <Li> Andy Williams (in a medley with "The Holiday Season"), on his 1963 album The Andy Williams Christmas Album </Li> </Ul> <Li> Jo Stafford on her album of the same title of the song Happy Holiday, this is the first time the song was released on a Christmas album in 1955 . </Li>

Bing crosby happy holiday other recordings of this song
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