Development
The Who's That Girl World Tour was musically and technically superior to Madonna's Virgin Tour, because she incorporated multimedia components to make the show more compelling. As the tour was confirmed, Madonna and her team started planning for it. Madonna wanted a show which consisted of theatrics, drama, dance and choreography in "full-force". Her publicist Liz Rosenberg commented, "She wants a visual impact that would knock people out. She was very determined about this. And she's the type that makes decisions quickly; If something doesn't work, she starts over. You'll see a different look this year, but it's still Madonna, still bigger than life." In order to engage herself completely and handle the grueling dance routines, she started attending aerobics classes at Hollywood health centre The Sports Connection. By the time the tour drew nearer, she hired a personal trainer, and her daily routine involved jogging, weight-lifting, dancing, gymnastics, trampoline, swimming and cycling. She started eating vegetarian food with plenty of protein and carbohydrate and avoided the sun. British funk band Level 42 was the supporting act of the tour. Madonna's image was that of a blond girl with soft curls, making a striking contrast with the firm, almost hard lines of her eye make-up and lipstick; the idea of her friend actress Debi Mazar.
For the costumes, Madonna collaborated with designer Marlene Stewart. She expanded on the idea of bringing her popular video characters to life onstage, reworking scenes from "True Blue", "Open Your Heart", "Papa Don't Preach" and "La Isla Bonita". For "Open Your Heart", Madonna reused the Stewart designed black bustier worn by her in the video, complete with tassels, golden tips and ribbing with fishnets on leg. Stewart's other designs included a Spanish style dress for "La Isla Bonita" and a gold lamé jacket for the "White Heat" sequence. The last dress of the show was visually amusing and, according to Madonna, was for "anyone that takes me too seriously, or imagined and I take myself too seriously." Inspired by Dame Edna Everage, the dress consisted of a hat strewn with fake fruits, flowers and feathers, jeweled batwing spectacles with heavy, black frames, a ruffled skirt and a bodice covered with objects such as watches and dolls and fishnets. The knickers were inscribed with the word "Kiss". Continuing her tradition of message clothes, she spelt out the phrase "You Can Dance" on her jacket, using the letter U, a can of soup and the word "dance" at the back.
Calling the show a "theatrical multimedia spectacular", Madonna wanted a huge stage with a central platform from which a flight of stairs descended. The central platform was flanked by two lower platforms, which housed the band and the musicians. A large video screen was suspended above the stairs, which descended during the show. Two projectors were situated at the front of the stage, which projected images of The Pope and President Ronald Reagan during the show. Patrick Leonard, who had produced True Blue, joined as the musical director for the shows. Instead of following every note on the records, Leonard encouraged the musicians to come up with new ideas for the songs. Hence a number of the old songs were rearranged, including introducing a medley of "Dress You Up", "Material Girl" and "Like a Virgin"—which contained a sample from the Four Tops song "I Can't Help Myself (Sugar Pie Honey Bunch)". American choreographer Shabba Doo was signed to choreograph the show. 13-year-old Christopher Finch was signed to play the part of the small boy from the "Open Your Heart" video, since Felix Howard, who played the original part, did not get a working license, and hence could not join the tour. Madonna wanted three backup singers, a team of male dancers and a succession of costume changes. She took inputs from her then husband, actor Sean Penn saying, "I really respect Sean's opinion. He has great taste and is a very brilliant man. When I was putting my tour together, it was always in the back of my mind: 'I wonder what Sean will think of this?' He's extremely opinionated and has really high standards, and that sometimes pushed me into making decisions I wouldn't have otherwise made." The title "Who's That Girl Tour" came to Madonna's mind during rehearsals one-day when she looked at a gigantic image of herself, projected on a screen on the stage. She commented,
"Oh god, what have I done? What have I created? Is that me, or is this me, this small person standing down here on the stage? That's why I call the tour 'Who's That Girl?'; because I play a lot of characters, and every time I do a video or a song, people go, 'Oh, that's what she's like.' And I'm not like any of them. I'm all of them. I'm none of them. You know what I mean.?"
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