- Awesome Music:
- "Rehab," her Signature Song.
- "Fuck Me Pumps" even gets people who don't usually like her music dancing.
- For her, singing a duet with Tony Bennett, one of her favorite artists and inspirations.
- Covered Up: Her version of "Valerie," originally by The Zutons, has not only become one of her most popular songs, but has covered up the original, which is particularly impressive as the original was a sizeable hit itself.
- Crack Pairing: In her short career, Amy only did four duets (that we know of as of 2011). So it's very jarring to know that Duet #4 is with none other than an artist over three times her age, and who outlived her entire life. Ladies and gentlemen, Tony Bennett and Amy Winehouse.
- Even Better Sequel: Whilst Frank was a best selling album and a critical success too, Back to Black was an international hit and is often regarded as one of the best albums of the 00's.
- "Funny Aneurysm" Moment:
- When Amy Winehouse was a guest on Nevermind The Buzzcocks, some of the jokes told by Simon Amstell were this.
- Harsher in Hindsight: "They tried to make me go to rehab; I said no, no, no." At first it was harsh due to her continued drug and alcohol problems after the song became a hit, then she died...
- Also, every joke that has been made about her being an unkempt drug addict. Doubles as a "Funny Aneurysm" Moment.
- Some of her sadder not waking up unhappy with life songs became this for her fans after she died.
- The music video of "Back to Black", which is about a funeral. Said funeral is to her heart. And even the end slate (which has since been removed in later releases of the music video) has the words "Rest in Peace Amy Winehouse's Heart". Brr.
- Never Live It Down: Though now averted in the face of Dead Artists Are Better, she was infamous for a while for her performance at a concert for Nelson Mandela's birthday where she decided to sing "Free [Blakey My Fella". At the time, he was in jail for assaulting somebody.
- While it's now been averted due to her passing, the topic of her publicized drug and drinking problem are still recurring.
- No Such Thing as Bad Publicity: While not a bad album by any means, Back To Black might not have sold so well if it weren't for her highly publicized drug addiction.
- Painful Rhyme: Amy rhymes 'players', 'say' and 'millionaire' in "Fuck Me Pumps", with millionaire pronounced 'millio-naya' to fit:
You don't like players
That's what you say-a
But you really wouldn't mind a millionaire
- Signature Song: "Rehab," easily the most famous of her songs.
- Tear Jerker: Songs such as "Love is a Losing Game" and "Back to Black," which have just been made worse by her untimely passing.
- Russell Brand wrote a really thoughtful article about her, her issues and her affect on culture.
- The Woobie: She basically is this in recent memory. She started off basically starting a revival of British music once again, but her drug and drinking problems ended up making her the press's next Britney Spears and just wouldn't leave her alone. The myriad of jokes and mocks about her problems didn't help matters (well.. it kinda did...) but it eventually just lead to her tragic death at the age of 27, making her fears of joining the "27 club" too and finally making people stop mocking her and realize what it lead to.
- Yoko Oh No: In a rare male example, Blake Fielder-Civil got a lot of this during his off-again-on-again relationship with her.