NOTE: I have watched up to the first seven episodes of season 6. So I apologize if there are any canon things that happened in the background that I missed in later seasons.  
—  
After many centuries I announce, the Background Six redesigned! I did a teaser for the redrawn Lyra and I’ve been pulling off redesigning the rest, but here it is! It’s only portraits, but in another century, I’ll make a full body.
 
Here we go, updated headcanons for these guys leggo!
 
Lyra Heartstrings: The de facto leader. An eccentric person, she often comes up with a dumb plan. She was a graduate of Celestia’s School for Gifted Unicorns and Canterlot School of Fine and Performing Arts. Her talent is playing harp-instruments, with the lyre being her favourite. Lyra was also friends with Twilight Sparkle at Celestia’s School and was Octavia’s rival in School of Fine and Performing Arts.
 
Bonbon: Lyra’s best friend and girlfriend. Although plain looking, she has an amazing vocal talent and had an extraordinary past. She used to be a secret agent and her real name is Sweetie Drops. When the bugbear escaped Tartarus, her agency disbanded and she moved to Ponyville to have a fresh start. Her talent is making desserts and candies. Bonbon and Lyra met when the unicorn got lost upon arriving at Ponyville.
 
Derpy: A friends of Lyra’s. The clumsy, yet lovable mail girl in Ponyville. She attended school in Ponyville and did Flight Camp in Cloudsdale, where she was bullied there for her clumsiness. Her talent is creating bubbles. Derpy was also childhood friends with Rainbow and Fluttershy during Flight Camp. Born and raised in Ponyville, she still lives with her parents and younger sister, Dinky.
 
Doctor Hooves: Derpy’s boyfriend and the only male of the B6. As Ponyville’s timekeeper, he often panics when he loses track of time. He also graduated from a university with a degree in sciences, which is a strong interest of his. His talent is knowing when something will come at a certain time. Other than the B6, Doctor doesn’t have a lot of friends and lives by himself. He and Derpy met when she crashed into him.
 
Vinyl Scratch: Also known as DJ-PON3, she is Ponyville’s local DJ. A night owl that likes to party. Although she was a high school dropout, she was able to graduate from Canterlot School of Fine and Performing Arts, where she met Lyra and Octavia. Her talent is composing EDM. Vinyl used to live in Canterlot with her parents until they kicked her out. She’s also good friends with Pinkie Pie.
 
Octavia Melody: Lyra’s rival and Vinyl’s best friend. Growing up in the high class, she is a sophisticated person. She graduated from the School of Fine and Performing Arts. Her talent is playing bowed-instruments, with the cello being her main. Octavia and Vinyl became friends after working together for a project. Living in Canrterlot her whole life, she is not used to the “rustic” lifestyle in Ponyville.
 
Golden Harvest: Derpy’s best friend. She often hangs with the B6, but most of the time she’s busy harvesting carrots. Having lived in Ponyville all her life, there’s nothing particularity interesting about her. Her talent is harvesting vegetables and is always perfectly ripped. Golden has known Derpy since childhood and is also well acquainted with Applejack and other farmers in Ponyville.