What started out as comedy ended up being something way more serious. During Nick Kroll’s appearance on The Late Show on Wednesday, September 27, to promote his new Netflix comedy Big Mouth, the actor shared a cringe-worthy photo of himself as a teenager. Not to be outdone, Stephen Colbert then shared a school picture of himself with braces and announced he would donate $1,000 to Puerto Rico relief efforts for each celebrity who posted a photo of themselves at a “very awkward, pubescent age” using the hashtag #PuberMe and #PuertoRicoRelief.
As widely reported, Puerto Rico has been devastated after hurricanes Irma and Maria ripped through the island. Maria was a Category 4 storm that crippled the island with severe flooding, damaged buildings and left the U.S. territory with no power. At least 10 people have been confirmed dead and at least three hospitals are without supplies and running water. The damage is estimated to be billions of dollars and it could take several months to reconnect power and essential services to the island.
Many celebrities, including Jennifer Lopez and Marc Anthony, have pledged to donate their own money and time to help fund hurricane relief. Several businesses including JP Morgan Chase, Verizon, Starbucks and Google have also donated.
Stars taking on Colbert’s challenge include Sarah Silverman, Reese Witherspoon, Jimmy Fallon and Sarah Michelle Gellar. Scroll through to see the hilarious pictures!
Stephen Colbert
"Nick Kroll asked me to post a pic of my awkward stage, but I never had one. So here's me lookin' cool as hell!" Colbert posted on Thursday, September 28.
Credit: Stephen Colbert/Twitter
Allison Brie
Hey @nickkroll & @colbertlateshow - post a pic from my most awkward years and you'll donate to #puertoricorelief you say?? Challenge accepted! #puberme#headgear #tbt#YOUREWELCOME
Credit: Alison Brie/Instagram
Conan O'Brien
"Hey @nickkroll and @StephenAtHome, this photo was taken the day I replaced David Letterman. #PuberMe #PuertoRicoRelief."
Credit: Conan O'Brien/Twitter
James Corden
Hello ladies.... and @nickkroll and @StephenAtHome, I'm James from High Wycombe, England. #PuberMe #PuertoRicoRelief
Credit: James Corden/Twitter
William Shatner
Hey @StephenAtHome will this do? I’m on the road. #PuberMe#PuertoRicoRelief
Credit: William Shatner/Twitter
Steve-O
When I started thinking about trying pot... @StephenAtHome @nickkroll#PuberMe #PuertoRicoRelief @colbertlateshow
Credit: Steve-O/Twitter
Skylar Astin
This kid just snuck into his first Rated R movie! #puberme#PuertoRicoRelief@StephenAtHome@nickkroll
Credit: Skylar Astin/Instagram
Sarah Silverman
Yo ma mensches @nickkroll & @StephenAtHome here's some sweet awkward #Puberme for #PuertoRicoRelief
Credit: Sarah Silverman/Twitter
Sarah Michelle Gellar
.@StephenAtHome .@nickkroll I present my 14 year old yearbook photo (before I discovered tweezers) #PuberMe #puertoricorelief
Credit: Sarah Michelle Gellar/Twitter
Samantha Bee
@StephenAtHome @nickkroll This photo brought to you by Sun-In ™ and my grandma’s Liz Claiborne separates. #PuberMe #PuertoRicoRelief
Credit: Samantha Bee/Twitter
Ryan Seacrest
Found this in the Connie Seacrest archives under “awkward phase” #puberme#puertoricorelief
Credit: Ryan Seacrest/Twitter
Kristin Chenoweth
Meet High School Kristin, @StephenAtHome and @NickKroll. #MadonnaPhasein full force. #PuberMe #PuertoRicoRelief
Credit: Kristin Chenoweth/Twitter
Kevin Smith
Dear @StephenAtHome: Here is my circa 1986 #PuberMe pic to help with #PuertoRicoRelief. At age 16, I'm not a clerk, not yet mallrat...
Credit: Kevin Smith/Twitter
Kathy Griffin
And you wonder why I didn't lose my virginity until I was 20... #PuberMe
Credit: Kathy Griffin/Twitter
John Oliver
Hey, @StephenAtHome, for your #PuberMe #PuertoRicoRelief effort, I give you...the nuclear option...
Credit: John Oliver/Twitter
Jimmy Fallon
Hey @nickkroll and @StephenAtHome here’s my #PuberMe #PuertoRicoReliefphoto. #SquadGoals
Credit: Jimmy Fallon/Twitter
Chelsea Handler
My awkward phase came in my early 40s. #PuberMe #PuertoRicoRelief@nickkroll @StephenAtHome
Credit: Chelsea Handler/Twitter