Award Snub: Her not receiving an Oscar 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).
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.
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.
LGBT Fanbase: Most especially with Gen-X gay men, but is also beloved of other generations and plenty of LGBT women.
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.
Never Live It Down: Her baffling attempt to take on a British accent during her marriage to Guy Ritchie as if people would just forget she was an extremely famous American.
Also the time she got inadvertently pulled down the stairs by her dancers at the Brit Awards. No capes!
She was widely pilloried for her It's All About Me attitude during her tribute to the recently deceased Aretha Franklin at the 2018 VMAs, talking mostly about how her own career was launched by singing one of Franklin's songs at an audition. The next day she tried to explain that she was just asked to say something about Franklin and didn't realize it was supposed to be a tribute, which just made everyone ask what the hell she thought was going on.
Nightmare Face: The "Nobody Knows Me" interlude in the MDNA Tour. It's essentially Madonna with snippets of people's faces superimposed onto her own, in addition to scribbles that make Madonna's face look skull-like. The results are unsettling, to say the least.
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", and "Music". 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 its Hotter and Sexier image along with the accompanying coffee table book Sex which resulted in the sales becoming weak when compared to her previous albums to the point that said 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 led to a Creator Killer for her to the point that she had a Career Resurrection with Bedtime Stories but it has looked back more fondly in recent years, with most critics now praising it for its adventurousness and for breaking down taboos surrounding female sexuality in pop music (even if doing so almost cost Madonna her career), with the video for "Rain" nowadays considered to be one of the greatest music videos ever made.
We're Still Relevant, Dammit!: A lot of her post-90's output smacks of this trope. While she has always been known for reinventing her image, her last few albums (especially MDNA) have been heavily criticized for pandering to modern-day trends without really doing anything new or unique. It's also worth noting that for the first 20 years of her career, she rarely collaborated with other big-name artists and had either distance or rivalry with most of her peers like Cyndi Lauper, Janet Jackson, and Whitney Houston. Nowadays she still doesn't interact much with the artists of her era, but has been aggressively seeking to share the spotlight with younger pop stars like Britney Spears, Nicki Minaj, and Ariana Grande, all of which have collaborated with her (Spears with "Me Against the Music", Minaj with "Give Me All Your Luvin'" and "Bitch, I'm Madonna" and Grande with the music video of "God is a Woman"), as well as trying to be Ms. Fanservice in her fifties and beyond. It all makes her seem less like the legend she is and more like an Amazingly Embarrassing Parent trying to party with her daughter's friends. Fortunately, Madame X appears to be turning this around.
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.