Entertainment Music John Mayer Turning 45 Is the Perfect Time to Obsess Over These Heavenly Throwback Photos Even his "awkward" teen years will make you swoon By Diane J. Cho Diane J. Cho Diane J. Cho was the Features Editor of PEOPLE Digital from 2019 to 2022. She worked at the brand for nearly four years covering news, features, human interest, evergreen, holiday gift guides and more. She launched the How I Parent and What It's Really Like to Be …. digital series and has interviewed several celebrities and influential leaders within the entertainment industry. Prior to joining PEOPLE, Diane worked at Bustle, VH1 and Complex. She received her bachelor's degree in Journalism from Rutgers University and her master's degree from Columbia Journalism School. People Editorial Guidelines Updated on October 16, 2022 09:20 AM Share Tweet Pin Email Trending Videos 01 of 11 Brooding Baby Instagram This little heartbreaker always had those big brown eyes. 02 of 11 Model Mode John Mayer It was 1988 when this priceless headshot was taken, and now we need a few copies to keep in our wallets. 03 of 11 Adorable Archive John Mayer/ Instagram The singer lovingly deemed this teenage hairstyle a "butt cut," but we beg to differ. 04 of 11 Boy Band John Mayer/ Instagram Here's an adorable teenage Mayer and the guys in his 1995 high school band. Sidenote: Wonder why his shirt screams the words "SOIL ME" in all caps? Mayer summed up his amusing fashion choice by simply saying, "What can I say? I was an interesting boy." 05 of 11 Manifest Destiny John Mayer/ Instagram The star clearly knew his calling from a young age and put in the work to make his dreams come true. 06 of 11 L8er Sk8er John Mayer/ Instagram "nighty night, haters," the singer captioned this #tbt from 2000. 07 of 11 Teenage Dream John Mayer/ Instagram Just an exceptionally talented 16-year-old and his guitar. 08 of 11 Fashion Faux Pas John Mayer/ Instagram "#tbt 2006. It was a different time for pants," the singer confessed, alongside this photo of him wearing flared jeans. 09 of 11 Ride or Die John Mayer/ Instagram His love for music runs so deep, he's been committed for life. 10 of 11 Hi, Gorgeous John Mayer/ Instagram This outtake from Mayer's first EP Inside Wants Out didn't make the cut for the cover, but really should have. 11 of 11 Hair Apparent John Mayer/ Instagram "#tbt the lost years (I highly recommend you get yourself a couple)," the star cryptically captioned this photo featuring his longer, flowing locks.