Lola- The Kinks
The Kinks were an English rock band during the late 60's and early 70's. In 1970 they released one of their biggest hits "Lola" a tale about a young man who has an encounter with a suspected crossdresser in q club in Soho, London. The writer of the song, Ray Davies, claims the song is based on a real experience of the band's manager, though alternate versions of the tale claim it was based on a real life experience of the band's drummer.
Candy Says- The Velvet Underground
One of my favorite songs on this list was written by Lou Reed. Reed had a fascination with the underground community of crossdresser and transwomen. "Candy Says" is a song sung from the perspective of one such transwoman. She explains the dissatisfaction with her male body and how society imposed a male lifestyle as a result. The chorus is a hopeful outlook on her transition and alludes to the freedom she feels from living as her authentic self. Reed wrote and performed a number of songs with transgender themes both in his work in The Velvet Underground and in his solo career. But this song, in my opinion, stands as one of the most beautiful musical representations of the transgender experience.
Dude Looks Like a Lady- Aerosmith
Probably one of the more popular and obvious entries on this list, it forever is ingrained into popular culture from its multiple appearances in many films involving transgender themes. Even without those inclusions, the lyrics speak for themselves...Dude looks like a lady. It apparently originated from a bar crawl between Aerosmith frontman Steven Tyler who was having drinks with Motley Crue frontman Vince Neil. The two were at a bar where all the staff were dressed as women, prompting Tyler to state "Dude looks like a lady".
Cherry Lips- Garbage
Garbage is a staple in 90's music. The band's discography is filled with song after song with LGBT themes. Among them, "Cherry Lips" is likely the most fun. It's operates as an anthem for a transgender woman to get out and strut her stuff and has frontwoman Shirley Manson instilling confidence and cheering her on.
The Look- Roxette
As far as I could find, this song doesn't really have any explanation or backstory that connects it to transgender themes. However, if you give it a close listen the lyrics strongly allude that the person being sung about is transgender. With bits like "walking like a man", "she's a juvenile scam", "she's a lover's disguise" and "she's a miracle man"... It's difficult not to assume that it's about a transwoman. Even if it isn't, it's a fun, poppy song with a fun beat. I like to turn it on while putting on my makeup every once in awhile to help accentuate "The Look"
Most people would recognize this song from it's inclusion in the movie American Pie. While it's catchy and upbeat, most people don't pay much attention to the lyrics. The second verse says "Dressed me up in women's clothes, and played with gender roles. Line my eyes and call me pretty". If that's not a blatant representation of transgender life, I don't know what is.
And that's 6 songs with transgender themes. Look for future posts like this one to expand your Trans playlist.