Live Performances
Madonna has performed "Holiday" on almost all of her tours namely, The Virgin Tour, Who's That Girl, Blond Ambition, The Girlie Show, Drowned World, Re-Invention, Sticky & Sweet and the MDNA Tour in 2012. In 1984, Madonna performed Holiday on the hit dance show American Bandstand with Dick Clark. Madonna then added it to the set list of her 1985 Virgin Tour. It was performed as the second song of the tour. The same year she performed the song at the Live Aid benefit concert in Philadelphia in July.
The Who's That Girl World Tour in 1987 had Madonna performing "Holiday" as the last song of the tour. Madonna performed an energetic version of the song, signalling the celebratory and wholesome nature of the song's theme. She sang the final chorus twice, and on some dates asked the audience for a comb so that she could fix her hair and finished the performance. Two different performances are found in Ciao, Italia! – Live from Italy tour video filmed at Stadio Communale in Turin, Italy on September 4, 1987 and the Who's That Girl – Live in Japan tour video filmed at Korakuen Stadium in Tokyo, Japan on June 22, 1987.
For the Blond Ambition World Tour in 1990, Madonna said, "I wanted to throw an old song for fun, and 'Holiday' seemed to be a universal favourite. In addition to that it's one of the only old songs I've done that I can still sing and not feel I've totally outgrown it." Performing it as a part of the encore, Madonna appeared on the stage in a polka-dotted blouse with matching flounces at the bottom of white trousers and hair in a top knot with a ponytail. The costume was adopted from a My Fair Lady dress and was designed by Jean-Paul Gaultier. Three different performances are found in the Blond Ambition – Japan Tour 90 VHS, the Live! – Blond Ambition World Tour 90 VHS and the Truth or Dare documentary. The performance included in the documentary was used as a music video to promote it. The performance received four nominations at the 1992 MTV Video Music Awards, including Best Female Video, Best Dance Video, Best Choreography in Video and Best Cinematography in Video, but did not win any of the categories.
In The Girlie Show in 1993, the song was performed in an alternate version as the second to last song of the tour. It had a military theme to it. Halfway through the performance Madonna paused the song for a military drill with the dancers and the audience. The performance met with strong reaction in Puerto Rico, when Madonna rubbed the Puerto Rican national flag between her legs in between the performance. For the Drowned World Tour in 2001 Madonna wore a fur coat, velvet fedora and a customised Dolce & Gabbana T-shirt which proclaimed 'Mother' in the front and 'F*cker' in the back painted in silver. This demonstrated her ghetto-girl appearance adopted for the song's performance.
In the Re-Invention Tour in 2004, the song was again performed as the ending song of the tour. The song was given a tribal feeling with Madonna wearing Scottish kilts during the performance. The performance started with Madonna and her dancers doing a dance routine in front of the stage, then Madonna going on the revolving tiers of the stage to sing the song as confetti fell from above. The performance was included in the I'm Going to Tell You a Secret live album and documentary. Stephen Thomas Erlewine of Allmusic commented that the performance "feels like they could fit the Eurotrash, campy retro-disco feel of Confessions."
The song was added to the 2009 leg of her Sticky & Sweet Tour. It replaced the song "Heartbeat" from Hard Candy and was used as a tribute to singer Michael Jackson who died a week, prior to the start of the second leg of the tour. As Madonna sang the song, a picture of a young Jackson appeared on stage, followed by a Jackson impersonator wearing garments in Jackson style. The music then switched to a medley of his songs, like "Billie Jean" and "Wanna Be Startin' Somethin'", and the impersonator worked through his moves, including the moonwalk as well as the spinning and gyrating. Madonna clapped her hands, swayed from side to side and jumped up and down while images of Jackson over the years flashed on a big screen. After the performance, Madonna told the crowd, "Let's give it up for one of the greatest artists the world has ever known," and the crowd applauded.
During the MDNA Tour, Madonna began performing a minimal version of "Holiday" after "Open Your Heart" starting on the second performance at Yankee Stadium on September 8.
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