Movie: Madonna: Truth or Dare

Release Date: May 10, 1991

Director: Alek Keshishian

Starring: Madonna

Tag Lines: “Like you’ve never seen her before.”

“The ultimate dare is to tell the truth.”

“See the truth. Madonna dares you.”

Relevance: In the Spring of 1983, watching MTV, a very common occurrence in my pre-teen and teenage years, I came across a video by a new artist named Madonna. The video for “Burning Up” was stylish and the song was a catchy dance bop that immediately grabbed my attention. It got a decent amount of airplay on the music channel as there weren’t a lot of videos at that time, but the song did not generate a lot of radio airplay especially where I lived. It did make it to the number three spot on the Billboard Dance charts, but I only seemed to hear the song when watching television. Little did I know that this tiny, sexy, attractive waif of a girl singing the song would become the most famous woman in the world as well as my queen.

My true blue Madonna fandom started that year. After “Burning Up,” she released both “Lucky Star” and “Holiday” and there was no looking back for me. I was completely sold. Her first album was one of my favorite cassettes to listen to as a teenager. Then in 1984, she exploded on to the scene with “Like a Virgin.” She went from pop star to pop culture phenomenon over night. With each passing album, song, video and concert, my love for her grew more and more. It wasn’t easy being her fan in the 1980’s (or any decade for that matter) as she was often criticized and ridiculed no matter what she did. That was even more true being a boy. I can’t tell you how many times I was insulted just for liking her. But I didn’t care at all. I loved her.

If you have been following my blog this year, you are well aware that Madonna was (is) my queen, my savior as well as the biggest influence in my life. I have written about her many times as ‘Madonna: Truth or Dare’ is her eighth and final film on my list of most influential, favorite movies of all time (see 215. Four Rooms, 177. Body of Evidence, 98. Dick Tracy, 94. Desperately Seeking Susan, 35. A League of Their Own, 30. Who’s That Girl and 20. Evita for the other seven). It is often hard to put into words why this five foot, five brunette, often blond, force of nature has had such an impact on me. The common short answer I usually gave was that I was just born at the right time. But there is a lot more to it than that, and ‘Truth or Dare’ summed it up most effectively.

If you read about ‘Dick Tracy’ (see 98. Dick Tracy), you already know that I saw Madonna’s “Blond Ambition World Tour” in Philadelphia, Pennsylvania in 1990. I was nineteen years old at the time and in complete awe as I was lucky enough to see the show second row from the stage. It was by chance that I got those seats and I wouldn’t know exactly how I got so lucky until I saw ‘Truth or Dare.’ The show was incredible for many reasons. The fact that I was in the same room as my idol, and so close to her was just the beginning. I also got a flower that she touched (I still have that pressed flower in my possession), and she smiled at me while singing “Sooner or Later.” I won’t bore you with that story again (see 98. Dick Tracy), but it was like I died and went to heaven, and Madonna was God.

HBO aired the “Blond Ambition World Tour” later that summer and of course I watched it (and recorded it on a blank VHS tape) with my family. The recorded tape was played over and over and over again as I took it away with me to college. I watched it with friends on many a Saturday night as we got ready to go out. That September, Madonna performed her now iconic “Vogue” performance at the MTV VMA’s that I also watched with friends, screaming and cheering at every dance move in my dorm room. Later that Fall, Madonna released “The Immaculate Collection,” her first greatest hits compilation including the new song (and new controversy) “Justify My Love.” I got “The Royal Box” version for a Christmas gift from my mom and remember being a bit sad after opening it. With that release, the “Blond Ambition” era was now officially over. I couldn’t have been more wrong.

On March 25, 1991, a day before my twentieth birthday, I watched Madonna perform “Sooner or Later” from ‘Dick Tracy’ during the Oscar telecast. The performance was astounding and the song went on to win the Academy Award for Best Song later that night. Madonna looked gorgeous with her date, Michael Jackson, and I remember staying up into the wee hours of the morning watching the footage of all of the after parties to catch a glimpse of the King and Queen. That was when the rumors started swirling about a new documentary movie about to be released that May about “The Blond Ambition Tour.” It was like a died and went to heaven, again.

‘Madonna: Truth or Dare’ premiered on May 10, 1991 at the Cannes Film Festival. It received favorable reviews, something Madonna had not received since ‘Desperately Seeking Susan.’ The film has since been noted as groundbreaking for its casual portrayal of homosexuality and its impact on reality television and celebrity culture. It was a commercial success as well and was the highest grossing documentary of all time until 2002’s ‘Bowling for Columbine.’ The film did have a wide release in theaters, but unfortunately not where I lived. After finishing my second year of college, I returned home for work during the summer. My usual theater that I frequented was not playing the movie, so I had to search for it in the newspaper. I found it playing in a theater forty minutes from my house. So one night in late May of 1991, I borrowed my parents’ car and headed to see ‘Madonna: Truth or Dare’ alone.

I knew I was going to enjoy the film, but I was floored by how much more I came to love and respect Madonna. The movie humanized her in a way that hadn’t happened before. She was motherly, loving, caring, bitchy, moody, angry, sad and extremely funny. I had always thought she was very humorous as we share the same sarcastic, ironic sense of humor, but her silliness came through like never before. She was a dork just like me. The film showed many sides of her personality and I fell in love with her all over again. Madonna was a force to be reckoned with. Being an introvert, she was the kind of person I wanted to be, strong, forthcoming and not afraid to go after what she wanted. I was the polar opposite.

Because of the film, I also got to see John Draper, her tour manager and the man that gave me the second row tickets in Philadelphia. I think that first time in the theater I said “Hey” out loud when seeing him. Madonna, not happy with critics and industry people getting tickets near and around the stage from scalpers, started giving those seats away to fans that did not have the greatest seats. I was one of those fans. Mr. Draper was the one that came up to me in Philly and there he was in ‘Truth or Dare.’

Leaving the theater that night, I knew that I had to see ‘Truth or Dare’ again. And I did. The second time I went with a friend of mine that was curious about the movie. She was a casual fan of Madonna and wanted to see what all the hype was about as well as what I had been blabbering about for weeks. We traveled the forty minutes to the little theater and I watched the movie again, this time watching my friend’s reactions watching the movie. There were many times her eyes were as wide as saucers and her jaw dropped a bit, but she was completely entertained. After leaving the theater, my friend became a bigger fan of Madonna and we made the trip back home singing “Express Yourself,” “Vogue” and “Holiday” at the top of our lungs.

‘Truth or Dare’ was released to Home Video via rental in October of 1991. I was back at college then, and rented it with friends. Most of them had not seen the film as it never played around them, so this was their first time watching it. They laughed, they cried and they too became more enamored by the blond pop goddess. It was difficult not to. That following holiday break I watched the movie again, this time with my family. One of those viewings was while we were waiting for Midnight Mass on Christmas Eve. I remember my mom making a comment about what a “great holiday movie” it was. Despite her comment, my mom was a Madonna fan. She didn’t like some of the things she did on stage (pretty much like Madonna’s own father), but she loved her music and loved how much I idolized her.

Now I would be remiss if I did not mention how this movie affected my own sexuality and coming out. You see, in 1991, I was a straight man. Now I know what you are thinking. Oliver, you liked Madonna and Broadway shows, you were gayer than a picnic basket. True. I do believe with all of my heart that I was born homosexual, but truthfully my authentic self was yet to be discovered and locked somewhere in my self-consciousness. I never had thoughts of homosexuality or contemplated living a gay lifestyle before 1995. Because I was a fan of Madonna, who was a champion for gay men and women before it was even cool or politically correct to do so, I was fully aware of gay culture. I was surrounded by it because of her as well as my love for theater. I had so many gay friends in college but as far as I knew, I was only an ally. It wasn’t until I finished college and got married did I start to feel like a part of me was missing. No longer being surrounded by gay men and women on a daily basis, plus Madonna, due to the backlash of “Erotica” and “Sex,” was going through a more subdued, less brash era, I started to question my identity. It might be a confusing concept for some to grasp, but that was how I discovered my true sexual self.

‘Truth or Dare’ depicted homosexuals as people, real, honest, human beings and that was not a common occurrence in the 1990’s. After coming out in 1998, I revisited the film that I then owned on VHS. I remember watching and re-watching the film trying to convince myself that everything was going to be okay. Between that film and listening to Madonna’s “Ray of Light” album, I somehow got enough courage to start living the life that I was meant to lead. It was a difficult, dark time and I barely made it out alive. I always joke that Madonna made me gay, but I also seriously comment that she also saved my life.

‘Madonna: Truth or Dare’ was more than just a movie for me. It may be just a chapter in the long career of one of the world’s most influential and popular performers, but it was one that I often re-read when I needed to laugh, cry, be entertained and reaffirm my humanity and purpose in life. Madonna is more than just a pop star to me. She is my longest relationship (thirty-seven years strong), the strength I need when I am at my weakest, the loudest cheerleader when I need a boost, the calmest voice when I need sympathy and the extrovert when I am at my shyest. There is no way I could ever repay her for everything she has done for me in my life, but one thing is I will always have her back and root for her until my last day on this planet. Long live the queen.

Today’s Thoughts: “I know I’m not the best singer and I know I’m not the best dancer, but I’m not interested in that. I’m interested in pushing people’s buttons, in being provocative and in being political.”

Some people believe in God, I believe in Madonna. A lot of people don’t get that sentiment and that’s completely fine. But I refuse to apologize for it. Madonna is my homegirl and always will be. Watching ‘Madonna: Truth or Dare’ today all alone was exactly what I needed. The movie (and Madonna) gives me life and the film is exactly what this almost fifty, unemployed man that barely survived 2020 needed today.

Reliving the “Blond Ambition World Tour” is always a treat for me. It is by far one of my favorite concerts of hers that I got to see. It is a spectacle and ‘Truth or Dare’ captures its essence nicely. However, it is the behind the stage scenes that I still find most appealing and entertaining. I love watching Madonna and her cohorts dancing, posing and living in that glorious grainy black and white footage. In 2019 Madonna made comments about the film. “I had no idea I was going to inspire so many gay men to A) give blowjobs to Evian bottles, and B) be free and take a stand and say ‘this is who I am, like it or not’. When I look back and watch that film, I am horrified by my brattiness, but I’m also proud that it gave so many people hope”. I couldn’t have summed it up better myself.

Believe it or not I did have one concern about watching this movie today. My mom passed away in April of this year and I have avoided listening to Madonna’s “Promise to Try” song from her “Like a Prayer” album. The song is prominently featured in one segment in the film. As Madonna visits her own mother’s grave, the beautiful ballad is played in its entirety. As I suspected, as soon as the piano started playing, I burst into tears. I couldn’t help it. Grief never really goes away and it rears its ugly head every so often, sometimes triggered, often not. At least this time I had Madonna to mourn with me.

‘Madonna: Truth or Dare’ also represents the twenty-fifth and final film to include male full frontal nudity. Yes, my “penis list” makes its final appearance here on my blog. I can’t think of a better film to have that honor, so thank you Carlton Wilburn. “It’s fucking blue!” You can check out the rest of that now infamous list here: 10. Schindler’s List, 16. Pulp Fiction, 32. Philadelphia, 39. Brokeback Mountain, 47. Fight Club, 92. An American Werewolf in London, 93. Angels in America, 105. American History X, 110. Shortbus, 112. A Clockwork Orange, 113. Weekend, 120. Sex and the City, 133. Porky’s, 139. Trainspotting, 144. Fargo, 183. Terminator 2: Judgement Day, 199. Six Degrees of Separation, 209. The Fisher King, 295. Being John Malkovich, 296. Wildcats, 332. The Crying Game, 335. Born on the Fourth of July, 343. Sideways and 357. Amadeus.

What more can I say about Madonna? Truthfully, I can go on and on. But I won’t. Let me just say that if you are not a fan, that’s okay. I forgive you. Some of us are just more enlightened than others. Both Madonna and ‘Truth or Dare’ are iconic and monumental in many ways. The film and the artist are important not only for the gay community but for humanity. Any time something or someone makes us think outside the box or makes us address issues we need to but don’t want to, is progress. Because of Madonna, we have made progress.

Thank you, Madonna.

Awards: National Society of Film Critics Award for Best Documentary (nomination).

Ways to Watch: YouTube, Google Play, Vudu, iTunes, DVD Availability.