"Happy Holiday" (sometimes performed as "Happy Holidays") is a popular song composed by Irving Berlin during 1942 and published the following year.
"Happy Holiday" was introduced by Bing Crosby in the 1942 film Holiday Inn, with The Music Maid and Hal and John Scott Trotter and His Orchestra, where it is performed in a medley with the title song. While it is commonly regarded as a Christmas song, in the film it is performed on New Year's Eve, and expresses a wish for the listener to enjoy "happy holidays" throughout the entire year.
The song helped to popularize the phrase "Happy holidays" as a common greeting during the Christmas and holiday season in the United States.
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.
Acoustix, on their 1999 album Cool YuleThe Carpenters (as part of a medley), on their 1984 album An Old-Fashioned ChristmasPerry Como (in a medley with "We Need a Little Christmas"), on his 1994 album Perry Como's Christmas ConcertPercy Faith, on his 1966 album Christmas Is...Jackie Gleason, on his 1956 album Merry ChristmasSteve Lawrence and Eydie Gorme, on their 1964 album That Holiday Feeling!Peggy Lee, on her 1965 album Happy HolidayLiving Strings and Living Voices, on their 1968 album White ChristmasThe Manhattan Transfer (in a medley with "The Holiday Season"), on their 1992 album The Christmas AlbumBarry Manilow (in a medley with "White Christmas"), on his 2002 album A Christmas Gift of LoveJohnny Mathis (in a medley with "Caroling, Caroling"), on his 1986 album Christmas Eve with Johnny MathisNelson Riddle, on the 1970 album Avon Christmas 1970She & Him (in a medley with "The Holiday Season"), on their 2016 album Christmas PartyMichael W. Smith (in a medley with "The Holiday Season"), on his 2014 album The Spirit of ChristmasJo Stafford, on her 1955 album Happy HolidaySarah Vaughan (in a medley with "White Christmas"), on the 1989 album Hallmark Presents Carols of ChristmasDionne Warwick, on her 2004 album My Favorite Time of YearAndy Williams (in a medley with "The Holiday Season"), on his 1963 album The Andy Williams Christmas Album