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#Madonna60 - A Countdown of My 60 Favorite Madonna Songs

From controversial choices to obvious picks, this is a look inside my lifelong Madonna fandom.

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August 16, 2018 marks the 60th birthday of Madonna, an artist who changed my life and shaped my upbringing as a gay man. The difference she's made in the LGBTQIA+ community cannot be quantified. From spreading awareness and reducing stigma around HIV/AIDS, to creating the Raising Malawi organization to benefit the African country of Malawi, her impact goes far beyond pop music.

Still, the Queen of Pop has an vast and vivacious catalog of hits and album tracks, and these are my sixty favorites. From songs that defined her legacy, to forgotten gems, I hope you'll enjoy this celebration of her music.


60. "Gang Bang"
Less a song than a visceral ride through Madonna’s psyche after her divorce from Guy Ritchie. It's so explicit that it couldn't even be edited to appear on the "clean" edition of the MDNA album.

59. "Over and Over"
Easily written off as a frothy filler track, the song’s lyrics explore Madonna’s can-do spirit, which cannot be broken. 

58. "Hey You"
An inspiring climate change anthem released for Live Earth. Simple and uplifting, this sweet-hearted song was wrongfully panned by critics. 

57. "American Life"

“Madonna attempts rapping” was the headline from this banger, but the real headline should have been her brilliant, scathing take on fame and George W. Bush’s post-9/11 America. Its banned and retracted original music video is one of Madonna's most profound artistic statements ever.

56. "Burning Up"
The quintessential "young Madonna" song. It's entirely fueled by the personality that made her the biggest star in the world, and led to her being dubbed "the female Michael Jackson" from the start of her career.

55. "Where’s The Party"
Just a fun song. You can't help but groove along.

54. "Don’t Stop"
This is such a low-key song... but when you're in its grasp, it's inescapable. I had this on repeat a couple summers ago.

53. "Spanish Lesson"
This pick will make a lot of serious Madonna fans roll their eyes - but to me, this is one of her most fun '00s tracks. A flirty, bubblegum pop moment with clever verse lyrics and a big chorus. 

52. "Take A Bow"
Madonna produced this with legendary R&B singer-songwriter Babyface, who later went on to collaborate with Barbra Streisand on her 2014 Partners album. Fittingly, Apple Music compares "Take A Bow" to a big Streisand ballad. 

51. "Deeper and Deeper"
One of the most unexpected and exciting moments of experiencing the Rebel Heart Tour live was hearing Madonna take on this '90s jam in a style faithful to the studio version. 

50. "Gambler"
Never released on a studio album or greatest hits collection, this forgotten Madonna hit remains beloved by woke fans.

49. "Secret"

48. "Die Another Day"
In my world, this is the best James Bond movie song of all time. 

47. "I’m Addicted"
The sputtering, trippy song that inspired the title of Madonna's MDNA album. The production on this one is insane. I'd love to have been a fly on the wall while Madonna and co. produced this. Or any song, really.

46. "Lucky Star"
The premiere bubblegum pop song, "Lucky Star" remains fresh and fun.

45. "Give It 2 Me"
While it was absolutely the wrong choice to follow-up "4 Minutes" as the second single from Hard Candy, "Give It 2 Me" stuns with its Pharrell-assisted beat and occasionally silly lyrics. Madonna fans were quick to call out P for reusing the drums in the 2013 song of the summer "Blurred Lines (feat. T.I. & Pharrell)" by Robin Thicke

44. "Amazing"
One of the best deep cuts that makes Music the wonderful album it is.

43. "Some Girls"
Another glittering moment from the misunderstood MDNA, this William Orbit collaboration is the sonic equivalent to a sputtering laser light show. Lyrically, Madonna presents a sassier take on her Millennial pop star competition with this one. 

42. "4 Minutes (feat. Justin Timberlake & Timbaland)"

A giant dance song with over 100 audio tracks used in its composition, “4 Minutes (feat. Justin Timberlake & Timbaland)” reminds me of listening to Hard Candy in a car full of high school friends.

41. "Fighting Spirit"
A Confessions On A Dance Floor box set bonus track that feels like it should have made the standard edition of the album. It's just that good. Listen if you haven't.

40. "Justify My Love"

39. "It’s So Cool"
This sarcastic bop is a look at Madonna’s cynical side, and a deluxe bonus track from her 2009 greatest hits album Celebration

38. "Nobody Knows Me"
The Re-Invention Tour performance of this is so brilliant:

37. "Celebration"

36. "Future Lovers"
One of the first songs that helped me accept myself as a gay man. 

35. "Unapologetic Bitch"
Another hit that got away.

34. "Papa Don’t Preach"
I remember first hearing this as a kid, and finding the subject matter scandalous.

33. "Live To Tell"

32. "Spanish Eyes"
I remember listening to the full Like A Prayer album for the first time on vinyl, and falling in love with this song.

31. "Human Nature"
As a huge Britney Spears fan, my first experience with this song was watching the Sticky & Sweet Tour performance of it where Britney appears in the video backdrops. 

30. Bitch I’m Madonna (feat. Nicki Minaj)
A crazy sendoff to ageist haters, this mammoth dance track also features one of Nicki Minaj's best rap verses ever. My favorite memory of this song is watching Madonna's insane performance of it on The Tonight Show.

29. "Revolver (feat. Lil Wayne)"
If marketed properly, this could have been a major US hit. Lil Wayne was at the top of his game at the time, and this song is a slice of pop perfection.

28. "Voices"
Part of what makes Hard Candy such an underrated album.

27. "Joan of Arc"
Madonna at her most vulnerable.

26. "I Love New York"
This first appeared as a rock & roll bonus track on the I'm Going to Tell You A Secret CD, before being rerecorded as a dance song for the Confessions On A Dancefloor album. 

25. "Girl Gone Wild"

24. "Love Song"
A lot of people don't know that Madonna collaborated with Prince on her 1989 album Like A Prayer. This is because his guitar work on "Like A Prayer," "Keep It Together" and "Act of Contrition," and vocals on "Love Song" are uncredited. Michigan native Madonna spoke about the chilly Minnesota winter experience recording "Love Song" at Paisley Park:

We were friends and talked about working together, so I went to Minneapolis to write some stuff with him, but the only thing I really dug was ‘Love Song.’ We ended up writing it long-distance, because I had to be in LA and he couldn’t leave Minneapolis, and quite frankly I couldn’t stand Minneapolis. When I went there, it was like 20 degrees below zero, and it was really desolate. I was miserable and I couldn’t write or work under those circumstances.
— Madonna

23. "Candy Shop"
Maybe it’s the bubbly drums, maybe it’s the fact she’s performed this non-single on her last three world tours. Who knows? It’s a major grower. Thanks, Pharrell!

22. "Rebel Heart"
A confessional, upbeat song that maps the journey Madonna had to take to become the Queen of Pop she is today. Inspired me to get my first tattoo, which was the Rebel Heart album logo. The demo version of this song has a catchy vocal hook in the background that repeats throughout. 

21. "Me Against the Music" - Britney Spears (feat. Madonna)
Madonna does the unthinkable: guest stars on a song. This track was complete when Britney played it for her, Madonna offered to make it a duet. The result is a wild meeting of the minds of two of pop music’s all-time greatest stars. I remember watching the MTV “Making the Video” special on MTV, and freaking out when I realized the VCR didn't record it properly.

20. "Material Girl"
This was the first '80s Madonna song I fell in love with.

19. "Love Profusion"
Featuring profound lyrics and experimental production, this song captures what it must feel like to be in the honeymoon phase of a relationship with Madonna.

18. "Open Your Heart"
Catchy, catchy, catchy. 

17. "Express Yourself"

 "Look it up" - Madonna

"Look it up" - Madonna

16. "Like A Virgin"
I can't help but think of this iconic moment:

 Photo: Billboard

Photo: Billboard

15. "Isaac"
This song has a raw power which cannot be denied.

14. "Sorry"
A dance floor stomper that beautifully picks up where "Hung Up" left off; it's no wonder its music video does the same.

13. "Love Spent"
On an album filled with references to her divorce from Guy Ritchie, this multi-faceted song stands out as her definitive statement on the subject. The abrupt transition midway through makes way for an almost entirely new song, and feels like an epiphany. 

12. "Holy Water"
A percolating pop banger that feels dangerous and lyrically provides an updated, distilled version of her career-long focus on Catholicism. The Rebel Heart Tour performance of this is worth the cost of the Blu-ray set alone. 

11. "Beautiful Stranger"
Described by Apple Music as “one of her brighter, deeper singles ever,” and I couldn’t agree more. This was the first Madonna song I was obsessed with in real time when it came out.

10. "The Power of Good-Bye"
It took me a while to mature to the point where I could fully appreciate this song. It's a gorgeous, supremely well-written song.

9. "Ray of Light"
Over 5 minutes of pure, enlightened pop bliss.

8. "Like A Prayer"
Controversial and powerful, this iconic pop power ballad reigns supreme as #1 on the majority of mainstream writers’ top Madonna songs lists, and I can see why. 

7. "Oh Father"

Madonna has explored her mother’s death throughout the years, but no other work is more candid or haunting than this largely overlooked ballad. Sia has a wonderful cover of this, too.

6. "Hung Up"

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You’d think the prominent ABBA sample would define the song, but Madonna’s superpowers ensure the track would be solid without it. 

5. "Devil Wouldn’t Recognize You"

The type of maturity and depth critics claim they want to hear in modern Madonna music, but seemingly ignore.

4. "Don’t Tell Me"

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Uses country music elements to speak to her biggest detractors, middle America, in a send off that is both powerful and universal. 

3. "Frozen"

 A still from the haunting music video.

A still from the haunting music video.

No other cut on “Ray of Light” showed more artistic growth than “Frozen,” an extremely atmospheric song that analyzes depression. 

2. "Vogue"

 Madonna with beloved backup singer  Niki Harris .

Madonna with beloved backup singer Niki Harris.

A historic track that sounds fresh today, “Vogue” effortlessly changed the world by starting conversations and offering the general public a glimpse into queer culture. 

1. "Music"

The Queen of Pop defines music itself in the ultimate ode to the dance floor experience. I had full-body chills during her Super Bowl performance of this.


What's your favorite Madonna song? Tweet me! @DerekPlease on Twitter.

"June Bops...!" Playlist

Our official June 2018 playlist is out now on Apple Music & Spotify.

 Photo by Derek

Photo by Derek

"June Bops...!" is the second in a monthly series of unique playlists curated by DerekPlease.com!

Stream the playlist on Apple Music

Also available for free streaming on Spotify

Enjoy a musical journey through different genres like pop, old school and R&B. There's a lot of surprises! Things like "Jungle Kitty" by Bebe Zahara Benet and "Thru Your Phone" by Cardi B transition surprisingly well. 

Stay tuned for next month's series installment, "July Jams"! Stream last month's "...May Flowers Mix" playlist here.


What's your favorite song on the playlist? Hit me up: @DerekPlease on Twitter, Facebook, Snapchat and Instagram

"...May Flowers Mix" Playlist

Our official May 2018 playlist is out now on Apple Music & Spotify.

 Photo by Derek

Photo by Derek

"...May Flowers Mix" begins a monthly series of unique playlists curated by DerekPlease.com!

Enjoy a musical journey through different genres like pop, country and R&B. Older songs like "Run Along" by Erika Jayne blend perfectly into newer tracks like "Ooh La La" by Tinashe.

Stay tuned for next month's series installment, "June Bug...!"

Stream the playlist on Apple Music

Also available for free streaming on Spotify

Flip Phone Superstar 2018: Michelle Visage Hosted A Night of Jaw-Dropping Drag

The May 6th competition at First Avenue beautifully showcased the talent and inclusiveness of the Twin Cities drag community.

It was described as the biggest Flip Phone event of the year.

Upon arrival, it was immediately obvious how excited everyone was; the line to get in was stretched long down the sidewalk on both sides of the iconic First Avenue venue. People of all ages were there, including a group of moms with their daughters, and cross-generational drag families. Minneapolis-St. Paul event promoter Flip Phone had another success on its hands.

The pre-show meet & greet with singer and RuPaul's Drag Race judge Michelle Visage included excited hugs, conversation, and autograph signings. When my husband Jacob and I had our turn, I thanked her for inspiring this blog's creation; I made it using SquareSpace after hearing advertisements on "RuPaul What's the Tee with Michelle Visage." Ru & Michelle later featured DerekPlease.com in a SquareSpace ad on episode 54 of that podcast. 

Thanks to all that, I'm attending RuPaul's DragCon as press on May 11, 12 and 13. Michelle was a sweetheart and invited us to bring our copy of her book to her DragCon booth to be signed. She also complimented Jacob's Todrick Hall hoodie, describing "Toddy" as being like an adopted son to her.

 Michelle Visage wearing a Cherry Moon pin 

Michelle Visage wearing a Cherry Moon pin 

Flip Phone Superstar 2018's large, diverse crowd included beautiful people of all varieties. There was a friendly atmosphere that seemed perfectly in line with event sponsor ThisFreeLife, an initiative working to end cigarette smoking in young LGBTQIA+ adults. Representatives from ThisFreeLife were on site offering free Michelle Visage posters, prizes, drink tickets, face paint and photo opps in exchange for a simple email list sign up. 

Gigi Berry's Cherry Moon pins had a booth on site selling a variety of fun, pop culture-inspired pins. This included pins inspired by Rihanna, Ursula from The Little Mermaid, '90s boybands, queer culture and Beyoncé.


Dragula season one contestant Meatball opened the show with a seriously impressive lip-sync performance. It began with a scathing spoken word clip from Designing Women character Julia Sugarbaker. The classic sitcom rant ends in the declaration, "that, just so you will know, and your children will someday know, was the night the lights went out in Georgia!" This led into an exciting performance of the country classic "The Night the Lights Went Out in Georgia."

Hostess for the evening Michelle Visage then walked on stage to thunderous applause. It was the type of reaction only a true LGBT icon would get at a queer event. Her hilarious opening monologue explained how the competition would work. 20 contestants would be scored based on one performance each; two finalists would later lip-sync for their life for the "Flip Phone Superstar" title and prize package. 

Visage joked that the prize package reminded her of RuPaul’s Drag Race season one; it included a $1000 cash prize, a $500 gift card for Sigma Beauty, a $100 certificate from Midwest Makeup, a beautiful Casa Glam wig worth $250, and a pair of luxury eyeglasses from Eye Bobs at Mall of America. 

Visage introduced the judges panel: Meatball; GO 96.3 radio host Giselle Ugarte; fashion designer Samantha Rei from season 16 of Project Runway; and Julia Starr, the 2017 winner of the Flip Phone Superstar title.

Flyer photos by Darin K

The contestant performances began with Lala Love-Iman performing a high energy Missy Elliot medley in a pink glitter jumpsuit. Mercedes Iman Diamond wore a gorgeous shoulder-padded costume while tackling “Bitch Better Have My Money” by Rihanna and “Blow” by Beyoncé. Local moon-pop musician Symone Smash It gave an amazing performance of her original song “Meet Me Online,” featuring live singing. Her LED eyelashes and rhinestoned... strap-on... gave the crowd life.

Drag king Dexter Maine-Love did a rousing lip-sync performance of Adam Lambert's Glee cover of "Marry the Night." Later, Rosie Bottoms came down a staircase to Lana Del Rey's cover of the Disney classic “Once Upon a Dream," before launching into Avenged Sevenfold's “Nightmare" - a first for Michelle Visage, who said she hadn't seen a queen perform a Sevenfold track before. 

Utica Queen stunned the crowd and judges' panel in full rag doll drag. Wearing a massive patchwork gown with her lips sewn shut, Utica conveyed the emotion of Sanna Nielsen's "Undo" completely non-verbally before finally ripping the stitches off her mouth for a ferocious lip-sync. There were major Sally from Tim Burton’s The Nightmare Before Christmas vibes as Utica teared at her rag doll limbs to expose her insides. 

Another showstopper was local favorite Tygra. I even saw people wearing her merch. She drove the crowd wild in a flawlessly executed, physically demanding rendition of Todrick Hall & RuPaul's viral smash "Dem Beats." Considering Michelle Visage considers "Ru" and "Toddy" family, it was a ballsy move for Tygra to do their current single in front of her. The risk paid off! Tygra's backflip and death drop-filled number only got one critique: the fact she was wearing sneakers.

Other gag-worthy moments included Lila Vera performing the brand new track “One Kiss” by Calvin Harris & Dua Lipa - on roller skates - and Puffy rapping the Ja Rule classic “Always On Time (feat. Ashanti)” live.

Judging was mostly positive, but some constructive criticism and playful shade never hurts. The audience lapped up all those moments.

All told, every performance was interesting. Performance styles ranged from classic solo numbers to layered choreography with dancers. There wasn't a dull moment in the night, which is quite a feat with so many acts in the mix. CIS queens in the lineup received special shoutouts from Visage, who admitted she's never identified as a CIS or "bio queen," but simply as a drag queen.

 Giselle Ugarte,  photographed by Darin K

Giselle Ugarte, photographed by Darin K

While the judges' final scores were tallied, Julia Starr gave her Flip Phone Superstar title step-down performance to a seriously underrated song, "Controversy" by Natalia Kills. Although released in 2013, the pop banger hauntingly fits Trump's America. It's a song truly ahead of its time, perfectly performed by Ms. Starr, who made it clear she is a force to be reckoned with. 

After that, the final two was announced: Utica Queen and Tygra. This made total sense, as they were the obvious crowd favorites of the night. It all came down to their epic “lip sync for your life” showdown. Song selection? Taylor Swift's "Reputation" album deep cut “I Did Something Bad."

Tygra served confidence with a tight lip sync and classic drag dance moves. Utica Queen performed as a murderous bride, and made her performance memorable. Shocking moments from Utica included slowly destroying a bouquet of flowers, pulling two bloody meat cleavers out from inside her dress, and revealing a blood-splattered outfit under her gown.

After the song ended, Michelle Visage humorously confessed she is not a Taylor Swift fan. She then asked the audience to cheer for the winner. Flip Phone used a decibel meter to accurately detect this, but the deafening cheers for Utica made it obvious - she stole the show, and the crown! After she received her title and prizes, the judges and competitors celebrated to "I Wanna Dance With Somebody" by Whitney Houston.

All in all, Flip Phone Superstar 2018 was an inspiring live experience that left me already looking forward to next year’s edition.


Be sure to follow Flip Phone across social media! Their Minneapolis-St. Paul events and drag brunches are must-sees.
Instagram@FlipPhoneEvents
Twitter: @FlipPhoneEvents 
Facebookhttp://facebook.com/FlipPhone
Snapchat: FlipPhoneMPLS
Official Website: http://flipphoneevents.com

Vinyl: Britney Spears "...Baby One More Time" Inside Urban Outfitters Stores

"They want more? Well I'll give them more" - Britney Spears

 Friend of the blog  @KevinMichaelT  submitted this photo.

Friend of the blog @KevinMichaelT submitted this photo.

Being the generous Princess of Pop that she is, Britney Spears is bringing "...Baby" back! Late last summer, pre-orders for the prized Limited Edition vinyl release of her iconic debut album "...Baby One More Time" sold out twice. 

The demand was unprecedented and Urban Outfitters mostly remained silent despite thousands of fans begging for more. Traditional media outlets even covered the frenzy. 

November 1, 2017, I was one of the first customers to receive the LP, having ordered with rush shipping. Fans such as myself experienced a lot of heat for being one of the lucky few to secure a copy at face value.

That was understandable, as it came to light that literally hundreds - if not thousands - of the 2500 were purchased by eBay scalpers. A single listing on eBay currently states over 100 copies have been sold for $99+. Crazy!

A "Sold Out" placeholder page for the album sat on Urban Outfitters website for months until just recently disappearing. 

Today, friend of the blog @KevinMichaelT found three copies under the "S" tab in a Toronto location. The photo above depicts the "Glory"-ous scene. When he said "you should have seen me run for it," I could literally see it in my head, because... same. He bought all three, and is shipping one to another fan - what a sweetheart!

Personally, I see this as Urban Outfitters leveling tilting the odds of getting a copy in favor of the fans. Another online listing (though possible) would definitely attract scalpers, but an in-store sale is lower profile and more likely to get into real collectors' hands. 

Our local Urban Outfitters does not have the coveted LP in stock yet, so this expanded release is likely still in its rollout stage. Stay tuned on Twitter for updates! 

Follow @DerekPlease on Twitter

UPDATE #1 - 3/7/2018 7pm CT - @LuisKrayenhagen confirms to DerekPlease that Urban Outfitters in Seattle, WA has also had the vinyl in stock recently.