By: Victoria Autocunas
April 17, 2026
Rapper Macklemore, AKA BEN, poses for his Guardian shoot (Source: Guardian Magazine).
Ben is the real name of rapper Macklemore, who most people know for the songs Thrift Shop and Can’t Hold Us. People never really took him seriously for Thrift Shop due to the silliness, but when you dig really deep into his catalog, he has so many meaningful songs.
I discovered Macklemore when I got tickets to go see Kesha on their collaborative tour in 2018, The Adventures of Kesha and Macklemore. He was supporting his GEMINI album, which was released a year before. They have a song together on that album called Good Old Days about growing up and how life changes, which is one of his more serious tunes.
No one seems to talk about his music even though he still releases music and tours, so that is why I wanted to review him as an artist. I have always enjoyed his music whether it was serious or not. I have been hooked on his beat since middle school and I think I forever will be. The following review will be his best songs—in my opinion—alphabetically (obviously not the whole catalog).
Ain’t Gonna Die Tonight (Ft. Eric Nally)- This upbeat and uplifting tune about living freely and feeling that way is from his GEMINI album from 2017. When I saw him in 2018, he opened the show with this big song. This is one of my favorites because of the nostalgia from that time in my life.
Brad Pitt’s Cousin (Ft. Xperience)- This song reminds me of the bus ride in eighth grade in the fall. BPC comes from the album, This Unruly Mess I’ve Made, when he was still working with the name “Macklemore and Ryan Lewis” before he was completely independent. This is just a silly song of Ben giving into how people think he looks like which is basically one of Brad Pitt’s Cousins.
How To Play The Flute (Ft. King Draino)- This is one of Mack’s silliest songs from GEMINI. I can’t tell if it’s a sensual innuendo or not. It seems to just be a song he wrote for fun that matched the vibe of the album. The music video for this came out during the time of his tour with Kesha. This is my favorite version of Macklemore for sure.
Willy Wonka (Ft. Offset)- Another massively silly Macklemore song. The beat is super fun and has always been one of my favorite Macklemore songs. Actually is my favorite ever. My mom even likes this song which is a plus!
Wing$- This song I really liked listening to on the bus to school when I was in middle school, so it brings back a lot of memories. It is a simple song about how he loved wearing Jordans growing up and the power it gave him.
Finishing Up and Ranking
Looking over all the Macklemore songs I like makes me remember all the middle school memories I have with them. I also realized I like most of his silly songs, which is sometimes a good thing because you can’t always take life too seriously, which is how I like to live, so it shows my personality.
You can listen to Macklemore on his YouTube channel or Spotify.
As an artist, I give Ben a 4.5 because of his authenticity in his music and realness as a person.