Award Snub: Her not receiving an Academy Award nomination for Evita, despite the almost unanimous opinion that she did a very good job and the fact that she won a Golden Globe for her work (the Globe nominations and wins tending to be a preview of the Oscars).
Her hit singles are this. Notable songs include "Like a Prayer", "Love Profusion", "Music", Like a Virgin", "Vogue", "Deeper and Deeper", "Hung Up", "Ray Of Light", "Frozen", and "4 Minutes".
Certain album songs equal the quality of her hit singles including "Impressive Instant", "Paradise (Not for Me)", and "Love Spent".
Madame X has received mostly positive reviews, with some calling it her finest record since Confessions On a Dance Floor.
After the light, pop sounds of songs like "Holiday," "Lucky Star," and "Borderline," "Live To Tell," a mature ballad recorded for the True Blue album and featured in the movie At Close Range caught everyone off guard, and remains one of her most popular songs.
Broken Base: Those who like Madonna doing dance music or more traditional ballad stuff, also every single era.
Erotica is something of a broken base, as the album has a lot of defenders who like to point out how the album got overshadowed by the title track controversy and Madonna's Creator Breakdown.
"Hard Candy" is likely the most debated out of her more recent work. Some loving it and others citing it was her all-time low.
"Gang Bang" gained popularity due to its Refuge in Audacity violent nature.
The last three songs on the standard edition of MDNA ("Love Spent", "Masterpiece", and "Falling Free") were the most critically-acclaimed songs on the album. It helps that they were produced by William Orbit, who also produced Ray of Light.
"Impressive Instant", which almost became the fourth single off Music.
Fetish Retardant: The video for "Human Nature". Also, the video for "Die Another Day".
However "Human Nature" was already kinda tongue-in-cheek
If "Where Life Begins" was trying to be a sexy tribute to cunnilingus, it failed hard. It sounds like an advert for KFC.
Growing the Beard: "Live To Tell" is generally considered the turning point in Madonna's career, as it was the song that had her go from a mall rat teenybopper that critics loathed, to a young adult who was capable of singing soulful ballads about serious issues of human survival and courage.
Heartwarming in Hindsight: Antonio Banderas showed up in Truth or Dare when he was a struggling new actor in America. He would later get one of his first big roles in the country alongside Madonna in Evita.
Hilarious in Hindsight: Madonna singing the line "Every breath, I'm deeper into you" in 1985's "Crazy For You" takes on a new meaning in 2007, when she was photographed carrying a strap-on as she left a hotel with then-husband Guy Ritchie.
Jerkass Woobie: The subject of "Frozen" sounds like a very greedy, hateful, misanthropic man. However, the lyrics make it clear he's miserable being this way, and the song is about how the protagonist hopes she can "melt" him and make him better.
LGBT Fanbase: Most especially with Gen-X gay men, but is also beloved of other generations and plenty of LGBT women.
Misattributed Song: "Baby Love" (no, not that one) by one-hit wonder Regina was commonly mistaken as being from Madge due to it's uncanny resemblance to her pre-True Blue output. In fact, it was written by Stephen Bray with her in mind, but when she declined it Regina was recruited to be a Suspiciously Similar Substitute. She's even made to resemble Madonna in the music video.
Narm: "Where Life Begins", a tacky ode to cunnilingus which sounds more like an advert for KFC. She even says "finger-lickin' good" at one point in the song.
Parody Displacement: Her cover of Don McLean's American Pie came out at the same time "Weird Al" Yankovic's parody of the original, "The Saga Begins," was on heavy rotation on Radio Disney, prompting many children to complain about Madonna doing an unfunny version of a Weird Al song.
The producer responsible for the Hyperpop-tinged sound of "Bitch, I'm Madonna"? A then-little known producer SOPHIE. It was one of SOPHIE's first mainstream tracks.
The Lenny Kravitz-penned "Justify My Love" was based around a sample of Public Enemy's interlude "Security of the First World". A reviewer believed that Insane Clown Posse sampled the Madonna song in ICP's "Bowling Balls", rather than the Public Enemy interlude.
"Hung Up" samples a riff from ABBA's "Gimme Gimme Gimme (A Man After Midnight)" — a rare honor from a band not known for allowing other artists to use their work.
Who's That Girl is an interesting case in that despite being a bomb and critical failure, her comedic timing was one of the few things praised.
Dangerous Game is another interesting case. The movie was the first production of Madonna's Maverick Picture Production Company, but she hated the finished product and opted to badmouth the movie in interviews and the like, much to director Abel Ferrara's dismay. Critics were generally on Madonna's side and panned the film... except for her performance in it, which was widely praised.
Signature Song: A lot of candidates, including "Like a Virgin", "Material Girl", "Like a Prayer", "Vogue", "Ray of Light", "Music", "Holiday", "4 Minutes" and "Hung Up". She ranks among the few musical artists and bands who are famous on their own and not solely as "the guys who did that one song", though.
Squick: Certain things from the Sex book - like say, the image of Madonna being fondled by an unattractive and elderly man. Also, the book features analingus.
"Falling Free" made many a fan cry. Especially near the end when she sounds like she's on the verge of tears.
An overlooked one due to falling on American Life, but "X-Static Process" seems to tell of Madonna having an existential crisis and speaks to moments of having doubts when you're alone or comparing yourself to others.
"I Fucked Up" has a sad and bitter vibe. Especially the part where she lists how things could have been.
"Joan of Arc" has so much of this with Madonna sounding desperate for comfort from a world of cruel press.
They Changed It, Now It Sucks!: Subverted in that Madonna is an artist who has made her career on successfully reinventing her image and sound over and over again.
Then again, there are a lot of people who would debate her success in reinventing herself over and over again as well, with some going so far as to thinking of her as a relic of the past desperately trying to stay relevant in the modern music world. Opinions wildly differ whether she is still actually successful or not.
Vindicated by History: Her fifth album, Erotica, faced huge backlash from Moral Guardians when it first came out, due to the Hotter and Sexier image brought by it and its accompanying coffee table book Sex. This resulted in the album's sales being weaker than her previous albums, to the point that the backlash (along with the poorly-received Body of Evidence, a Star-Derailing Role for her as an actress, and the infamous 1994 appearance on The Late Show with David Letterman) almost became a Creator Killer for her. However, most critics now praise it for its adventurousness and for breaking down taboos surrounding female sexuality in pop music, with the video for "Rain" nowadays considered to be one of the greatest music videos ever made.
What Do You Mean, It's Not for Kids?: She attracted a HUGE fanbase of young girls when she first became popular in the '80s and many young girls would try very hard to make her look, from her long hair full of messy curls to wearing her lace fingerless gloves. And while a lot of her earlier singles (e.g. "Lucky Star" and "Material Girl") were rather harmless, sugary sweet pop flavor, her image was very sexualized and some of her other songs (e.g. "Burnin' Up" and "Like a Virgin") were rather erotic in nature - for the times, at least.