10 Best Songs About Not Being Good Enough

Jealousy, jealousy – Olivia Rodrigo 

Sad songs had something of a resurgence during the age of the coronavirus pandemic, and few musicians embody this more than former Disney Channel star turned singer, Olivia Rodrigo.

Her debut album SOUR was filled with irreverent pop punk jams from top to bottom. One of the biggest of these hits was “jealousy, jealousy”, where Rodrigo catalogues all of the things that make her feel inadequate even though she knows they shouldn’t. 

 Cute Without the ‘E’ – Taking Back Sunday 

Taking Back Sunday led the charge as emo bands took popular music by storm in the early 2000s. They made it big with “Cute Without the ‘E'”, which is a completely over the top anthem of heartbreak where the singer talks about feeling completely worthless after losing a lover.

MTv was so unprepared for the sensational, self-deprecating language that they famously edited the lyrics and music video when they first appeared on the station.

What Hurts the Most – Rascal Flatts 

Like most country songs, “What Hurts the Most” is a dreary-sounding song about lost love.

However, Rascal Flatts puts a spin on this template by telling the story from the point of view of a man who is reflecting on how he could have been better and how it might have helped him hang on to his loved one. 

I Fall Apart – Post Malone 

In the first words of “I Fall Apart”, Post Malone literally bemoans that “She told me that I’m not enough!”.

This emo rap song was a definite change of pace for the rapper who is known for his upbeat club songs. Post Malone has said that he wrote this song as an homage to emo rappers he admired when he was coming up in the music industry, like Lil’ Peep.

Please Don’t Go – Mike Posner 

Mike Posner went from mixing beats in his dorm room at college to an international recording star almost overnight with a rash of hit songs.

While most of these tracks were about partying and pursuing women, “Please Don’t Go” is a heartfelt plea to a lover that is determined to leave him behind.

This darker single among Posner’s early successes was a sign of things to come as his later music was thoroughly emotional and introspective.

Bad at Love – Halsey 

Pop singer Halsey burst onto the scene in the mid-2010s with her gritty and honest lyrics.

In “Bad at Love”, she pours her heart out lamenting about the various lovers that she has let slip away due to her own poor decisions. She commits to continue trying to find love, but wonders if she will ever be good enough to deserve it. 

Be My Escape – Relient K 

When it comes to the emo slash hardcore slash pop punk craze that dominated rock music in the 2000s, tons of bands released single tracks in the genre to get in on the action, even if it didn’t necessarily fit their general sound.

“Be My Escape” by Relient K is just such a one hit wonder. It tells the story of a person who finds themselves stuck in bad place in life and wondering how they ended up there. 

Parents – YUNGBLUD 

Pop singer YUNGBLUD is the perfect embodiment of the Gen Z angst occurring as a generation of people reaches adulthood and finds their prospects less than exciting.

“parents” takes this theme in casts it in YUNGBLUD’s own struggles with being accepted as a member of the LGBTQ+ community. He wonders how someone like him will ever be seen as good enough by society.

Turn to Hate – Orville Peck 

Country singer Orville Peck brings a sound that is both twangy and classic, but also hip in terms of its lyrical content.

“Turn to Hate”, from Peck’s breakout album Pony, is a sad song about how Peck’s desire to be a free spirit in his youth has left him on the outside looking in.

Despite the fact that he often feels lonely and inadequate, he fights to prevent himself from becoming a truly hateful cynic. 


When it comes to songs about not being good enough, few musical artists have taken it farther than the late emo rapper XXXTENTACION. The master of self deprecation was known for writing song after song about his own rejection and inadequacy.

In “SAD!”, he emotionally explains to his former lover that he is an anxious and insecure mess who can never do the right thing and is unworthy of love. 


Born and raised in Austin, David is a dedicated writer and avid fragrance lover. When he's not trying out perfumes, he enjoys traveling and exploring new restaurants.

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