16 Songs About Messing Up

Last Updated on: January 5, 2025

1. Trey Songz – Smartphones

The single is about Trey Songz getting caught cheating because of an accidental pocket dial that led to his girlfriend listening in on his sexual affairs with other women. He needs to figure out an excuse so as to try and save their relationship.

 

2. Jason Derulo – Whatcha Say

The song is an apology by a man who regrets cheating on his girl and has now been caught. Jason revealed that it is about his brother who called him one day and shared that he just cheated on the girl he loves so much. The story was so inspirational that he went into the studio and came up with a track. In the end, everything worked out for his brother.

 

3. Akon – Sorry, Blame It On Me

Akon did the song to apologize to the public after footage of him surfaced and in it, he was dancing raunchily with a 14-year-old girl. He was on tour at the time with Gwen Stefani and didn’t have time to respond to the incident. The girl came on stage for a grinding competition and her winning prize was getting dry-humped by Akon.

 

4. T.I feat Chris Brown – Get Back Up

In the song, T.I. asks the public to understand that he makes mistakes just like anyone else and he is willing to start over and make things right. At that point, he had been arrested for possession of unregistered machine guns and silencers. He also adds that when you are pushed down, you have to get back up yourself.

 

5. Halsey – Sorry

 

 

6. Trey Songz – Fumble

In this track, Trey Songz regrets breaking the heart of a girl who did everything he asked for so that they could be together. He couldn’t let go of his playboy lifestyle and settle with her. He is now regretting letting her go and feels he will never love anyone the way he loved her.

 

7. Taylor Swift – Back To December

The song is part of the album Speak Now (2010). It peaked at #6 on the Billboard Hot 100 chart and went ahead to win two BMI Awards (Publisher of the Year & Award Winning Songs) and a Teen Choice Award for Choice Break-Up Song. Taylor revealed that she wrote the song on a napkin in an airplane bathroom.

In an interview with Comcast, Taylor stated that this was the first time she had even apologized in a song. It was about a person who was incredible to her while they were in a relationship. However, she stated that she was careless with him. The guy was Taylor Lautner.

 

8. Bruno Mars – If I Knew

The song is about one of Bruno Mars’ ex. He speaks about how if he would’ve known that she wanted to come back to him he wouldn’t have done things the way he did. He adopted a playboy lifestyle sleeping with many different women thus making things less special with this girl.

 

9. Justin Bieber – Sorry

This is an upbeat anthem about asking for forgiveness. Bieber said the song was partly about an apology to his ex-girlfriend Selena Gomez and was also more of a general apology to the world for his mistakes.

The song debuted at #2 on Billboard’s Hot 100 chart and was able to dethrone Adele’s ‘Hello’ from the number one spot after 10 weeks.

 

10. Jay Z – 4.44

The song has been regarded as an open apology letter to his wife Beyonce. He raps about how he was a bad husband and the possibility of cheating on her. He states that it took the whole experience of getting their children to make him realize how important she was in his life. He states this about the song:

‘4:44’ is a song that I wrote, and it’s the crux of the album, just right in the middle of the album. And I woke up, literally, at 4:44 in the morning, 4:44 AM, to write this song. So it became the title of the album and everything. It’s the title track because it’s such a powerful song, and I just believe one of the best songs I’ve ever written.

 

11. Stormzy – Lessons

This is a song about Stormzy’s ex May Jama, a TV and radio presenter. They split back in 2019 and speculations are that he was unfaithful to her with fellow singer Jorja Smith. Stormzy denied the claims and stated he only disrespected her. He stated:

I was out, moving stupid, I was like, I was in clubs, not giving a fuck about, like, who I was talking to, or what I was doing, or who I- like, and, yeah, end

 

12. Usher – Confessions Part 2

The song is part of Usher’s fourth studio album Confessions. Lyrically, we hear Usher try to confess his infidelity and that he got another woman pregnant. He barely even knows the woman and is asking for forgiveness.

Usher is singing as a character inspired by his producer Jermaine Dupri who experienced the whole situation.

 

13. Jessie J – Nobody’s Perfect

The song is off her debut studio album Who You Are. Jessie J says sorry for her words which hurt someone who was important to her. She explains why she ended up saying the hurtful things she said. She emphasizes that no one is perfect so she deserves to be forgiven.

 

14. Cher – If I Could Turn Back Time

The song was released in 1989 and was seen as a major comeback for Cher in the late 1980s. It was part of her 19th studio album Heart of Stone. Lyrically, the song talks about wanting to find a way to turn back time and take back the words that she said. She didn’t mean to hurt him and wished she wasn’t too proud to apologize when she had the chance.

 

15. Eminem – Headlights

In the song, Eminem issues a public apology to his mom since the two have never really gotten along. She has been a target in some of the songs such as ‘Cleaning Out My Closet’ and ‘My Mom’. In an interview with Sway Calloway, he had this to say about the track:

It was one of those things that’s bothered me for a little bit. It was one of those things that I needed to get off my chest. So I don’t really have anything to elaborate or expand on that record other than everything that I needed to say, I put on that record.

 

16. Bruno Mars – When I Was Your Man

This is an emotional song from Bruno Mars’ second studio album Unorthodox Jukebox which was released in 2012. He said on many occasions that this is his most difficult song to perform because of the lyrics and meaning.

The song starts with Bruno Mars stating the different changes he has felt since his ex left and the heartbreak he feels each time their friends talk about her. He goes into how he regrets not doing enough for her when he had the chance and ignoring the things she desires. She now moved on to someone else who is doing those things. He feels he will never be able to make things right for her and this haunts him every day.

Even though he still desires his ex, Bruno hopes that the new man his ex is seeing make her happy the way he should have done when he was with her.