Putting together a list of ten hip hop regret about love songs is easier than it sounds. Rappers talk about all sorts of topics and it is surprising how many songs they make about love. It might not be “boy meets girl/boy loses girl” kind of love all the time, but passion holds true whenever the heart bears the weight of regret. Listen to these rappers lay their hearts on the line and you just might cry.
- “Make the Song Cry” by Jay-Z. This rap song is an apologetic ballad in the spirit of the best love songs. Full of regrets, self-reflection and sorrows, it puts hip hop in an entirely different category. Jay’s insightful lyrics and the soulful female vocals put this song over the top.
- “Passing Me By” by The Pharcyde. The striped down sound of this groove laced song fits its theme of unrequited love perfectly. A recollection of being overlooked by the high school hottie, this ballad wallows in the regrets of adolescent crushes.
- “Ms. Jackson” by Outkast. Outkast lays out their regret in the hook of this song with an open apology to Ms. Jackson for the troubles brought upon her daughter. A cool tribute to the Baby Mama’s mama’s.
- “I Miss My Dawgs” by Lil Wayne. Who says love is only between a boy and a girl? Wayne bares his feelings in this song about missing his former bandmates. Choked up with the regrets of ego and bad deals this is an honest appeal to former friends.
- “Brenda’s Got a Baby” by Tupac. The immortal rapper tells a sad tale of preteen pregnancy in this song about a young girl and her choices. Full of woe and regret, this song is true social commentary.
- “Tie My Hands” by Lil Wayne. This heartfelt rap ballad details the social struggles and calamities experienced by the residents of New Orleans after Hurricane Katrina. Introspective and relevant it shines as one of hip hop’s most hopeful tunes and is a true love song to the residents of N’awlins.
- “Little Girl Gone” by Devin the Dude, Bun B, & Lil Wayne. This track describes the life of a young girl who slipped through the cracks, like so many in urban communities. Lost and feeling unloved, she searches in all the wrong places.
- “Runaway Love” by Ludacris. Another song describing, in detail, the trappings that young girls can find themselves in. A graphic depiction of drug use, physical and sexual abuse, this song serves as a cautionary tale to runaway teens.
- “So Many Tears” by Tupac. A shout out to the gone and departed homies, Pac lays it out for the lost lives of his partners.
- “I’ll be Missing You” by Puff Daddy featuring Faith Evans and 112. This famous tribute to the Notorious B.I.G. samples The Police’s “Every Breath You Take,” to sublime effect. A true love song to a fallen friend that will be forever missed
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