Fifty-five years is a long time. Especially when the pressure is constantly on you to innovate and impress with each new incarnation. For Madonna, this has never been an issue. Her age has been something people have attacked since she hit 30. Two years after, in 1990, she toured the world on one of the most rigorous concert performances of her career--and in history--Blond Ambition. And so, to say that Madonna relishes proving her detractors wrong is something of an understatement. Below are fifty-five life and career events that everyone assumed would break this learned Leo. Madonna lost her V card around the time that she looked like this (#swag).

1)Losing her virginity at 15 (which she jokingly quipped was a career move)

While performing in Godspell, Madonna ripped her pants off to reveal nude hued tights--foreshadowing her innate ability to shock with her sexuality.

2) Performing in her high school's production of Godspell wearing flesh-colored tights

Taken while Madonna attended the University of Michigan, where it was immediately evident her ambition could not be contained.

3) Dropping out of the University of Michigan on a scholarship

Moving to New York in a destitute state may have been invigorating for the soul, but not so much for the stomach.

4) Moving to New York with approximately 35 dollars

Madonna in the early days of synagogue squatting (presaging her love of Kabbalah, perhaps).

5) Squatting in an abandoned synagogue with then boyfriend Dan Gilroy

One of the tamer photos of Madonna's nude modeling career.

6) Posing nude for extra cash (though she wouldn't know how much it would come back to haunt her later on)

Making a living, the honest way.

7) Working as a coat check girl at the Russian Tea Room--exhibiting her undeniable blue collar Midwestern ways

Camille Barbone (right) fell easily for Madonna's charms, even going above and beyond the call of managerial duties by paying for her dentistry.

8) Getting sexual with her lesbian manager, Camille Barbone

http://youtu.be/3ePfBBawcP4

9) Auditioning for and failing to get on Fame

Hangin' with Patrick.

10) Performing as a backup dancer for Patrick Hernandez

http://youtu.be/OGYVJUMB4-8

11) Writhing around in a wedding dress at the 1984 MTV VMAs

Two Leos: It could never work

12) Marrying Sean Penn

Madonna and Maripol: A match made in fashion heaven.

13) Shedding her signature street urchin image--plastic bracelets, crucifixes, etc.--so carefully cultivated by Maripol

http://youtu.be/RkxqxWgEEz4

14) Releasing a song about teen pregnancy

At the Don't Bungle the Jungle benefit

15) Galavanting with Sandra Bernhard so frequently that they, along with Jennifer Grey of all people, became known as the Snatch Batch

http://youtu.be/yhX89dDoAw4

16) Making Shanghai Surprise with Sean Penn

http://youtu.be/mpU6ueRX0kA

17) Starring in a David Mamet play, Speed-the-Plow, during her down time in 1988

http://youtu.be/h8qtsUaoVak

18) "Selling out" by signing a five million dollar ad campaign with Pepsi

Basking in the warm glow of a burning cross.

19) Releasing the "Like A Prayer" video, featuring, among other incendiary imagery, burning crosses--which then prompted Pepsi to pull the plug on their deal

Madonna as Hortense Hathaway, a precursor to her role in Shadows and Fog.

20) Bloodhounds of Broadway (also starring Jennifer Grey)

A romance that couldn't last.

21) Divorcing Sean Penn amid rumors of domestic violence

Gracing one of many covers during their time together.

22) Permitting herself a brief dalliance with Warren Beatty while working on Dick Tracy

http://youtu.be/4_J3s1sTIng

23) Having the Pope urge Italians—and all good Catholics—to refrain from attending the Blond Ambition Tour for its sexual/religious motifs 

http://youtu.be/Np_Y740aReI

24) Releasing the video for “Justify My Love,” only to have it turn out to be her first ever offering to get banned from MTV

The two would eventually appear together in the Sex book.

25) Dating Vanilla Ice

http://youtu.be/fYS2I45tj4A

26) Truth or Dare, which served to blur the lines between what Madonna wants us to believe and what is actually real about her persona

The original edition of Sex came in this mylar wrapping.

27) The Sex book, including diary entries from the perspective of Madonna’s alter ego, Dita

http://youtu.be/WyhdvRWEWRw

28) The backlash that resulted from Erotica, solidifying public opinion of Madonna as an oversexed, self-destructive dom type

http://youtu.be/WJfPgjR_czA

29) Starring in Body of Evidence on the heels of the two aforementioned projects

Madonna took her knack for offending people to new heights with The Girlie Show, parts of which Gene Kelly helped her choreograph.

30) Rubbing the Puerto Rican flag between her legs while touring for The Girlie Show in 1993

http://youtu.be/4TgqquzI6-A

31) Her profanity-laden appearance on David Letterman in 1994

A phase in which Madonna was also okay with drinking out of a paper bag.

32) Dating Dennis Rodman

A shared love of fitness couldn't keep them together.

33) Mixing business with pleasure by dating her trainer, Carlos Leon

Not everyone was okay with Madonna having Lourdes without marrying Carlos Leon.

34) Having a child out of wedlock in 1996

One of the many examples of M's love for this sect of Judaism.

35) Newfound spirituality and allegiance to Kabbalah

http://youtu.be/XS088Opj9o0

36) Being accused of plagiarizing 1998’s “Frozen” from Salvatore Acquaviva, a Belgian songwriter 

http://youtu.be/jmec0w5G4xA

37) The Next Best Thing

http://youtu.be/sQVieEO6GuU

38) Remaking Don McLean’s “American Pie”

http://youtu.be/qYwgG2oyUbA

39) Collaborating with then husband Guy Ritchie to make yet another banned video on MTV, “What It Feels Like For A Girl”

http://youtu.be/TQnb0iNM3cc

40) The lack of pomp and circumstance on her second greatest hits collection, GHV2

http://youtu.be/wv4grEwufV8

41) Turning Lena Wertmuller’s seminal Italian film, Travolti da un Insolito Destino… with Guy Ritchie into Swept Away—though it really isn’t as terrible as everyone makes it out to be.

http://youtu.be/kFEWeoWNvcw

42) Starring in the West End play Up For Grabs during her British phase

http://youtu.be/dSLDJDUw75o

43) American Life, her lowest selling album, but one of her best works

http://youtu.be/s4yN-iez8XY

44) Becoming a children’s book author

http://youtu.be/Wi8Zh1EGtLU

45) Hanging herself on a cross during a performance of “Live To Tell” on The Confessions Tour

http://youtu.be/Wl-m6V--jJM

46) Adopting a Malawian child named David Banda, a move everyone considered to be conveniently “chic”

The "tell-all" book that didn't tell much at all.

47) The tell-all book written by her brother, Christopher Ciccone, in 2008

http://youtu.be/9Sig62vyUF0

48) Divorce from Guy Ritchie, after which he was purported to have said that being with her was like “cuddling up to a piece of gristle”

http://youtu.be/X6XIxqGCJLc

49) Her third directorial effort, W.E.

http://youtu.be/UJuYjtp70jc

50) Now famously calling Lady Gaga “reductive” when asked about the singer’s “Born This Way,” which bears a strong resemblance to “Express Yourself”

http://youtu.be/cItHOl5LRWg

51) “Give Me All Your Luvin’”, the first single from her twelfth studio album, MDNA

http://youtu.be/LOuV03CNGxU

52) Referencing the use of molly at the Ultra Music Festival in Miami, causing DeadMau5 to deride her on Twitter (but whatever, fuck him)

http://youtu.be/m2y9j-v_OWY

53) Contention in Malawi over her involvement in building schools for girls after officials stated Madonna was embellishing the true nature of her contributions

http://youtu.be/-FZz6jsJRqU

54) Dating a Brahim Zaibat, her backup dancer, 29 years her junior

http://youtu.be/lpNZN5rWIF0

55) Facing an all-out ban from Russia in the wake of her support for Pussy Riot while in Moscow and St. Petersburg for her MDNA Tour.

Naturally, in the span of just one year, there could likely be another fifty-five things to add to this list. But I’ll save that for Her Madgesty’s 110th birthday.