When Bear Grylls from Man vs. Wild was matched with a Redditor from Iowa in 2011, he sent her an autographed photo, a copy of his autobiography, seasons three and four of Man vs. Wild, two Man vs. Wild video games, and a survival kit. It is unconfirmed what Bear drank right before sending the package, but we bet you could take a pretty good guess.
A Redditor named Rachel's jaw hit the floor when she opened her mail to find a personalized gift from none other than Bill Gates. He had sent her a travel book, a stuffed cow, and notification that he had made a (presumably substantial) donation in her name to Heifer International, a charity that fights poverty. As proof, he also included a photo of himself. Our pity goes out to whomever had to send a gift to Bill Gates that year. Can't be an easy guy to shop for.
In last year's Secret Santa exchange, Shaquille O'Neal was excited to share his favorite interest: himself. So, along with a Star Wars book and some postcards, Shaq sent his Reddit match a large, framed, autographed photo of himself that looks like it was taken in a mall studio for Senior Picture Day. You gotta hand it to Shaq - even with all his millions, he knows how to reach out to the youth of America.
Mark McGrath's gift was a head-scratcher. When he found out that his match's favorite show was RuPaul's Drag Race, the Sugar Ray frontman tracked down an autographed photo of one of the show's judges, Michelle Visage. The amazing thing? That's ALL he sent! McGrath didn't even throw in any of his own merch. Thus, for Redditor 23port, this signed photo of a TV judge sent by Mark McGrath will forever go down in history as the most random gift ever.
Les Gold, the dude from Hardcore Pawn, is a pretty thoughtful secret Santa. While he did send the customary autographed photo of himself, he also sent along a huge stack of Pokemon trading cards to his giftee. Now that we think about it, we suppose he could have very easily sent some gold from that jewelry shop of his, too. Eh, the Pokemon cards will probably better appreciate in value anyway.
For Reddit's Arbitrary Day exchange in 2011, Jimmy Fallon decided that, instead of just buying his match something, he'd do one better and have The Roots improvise a personal song for her. So, Jimmy read a list of her interests to Tariq, and then turned the mic over to the Late Night house band for the jam. You can't help but pity whomever got matched with her next year. Tough act to follow.
Stephen Colbert spearheaded Reddit's 2012 Exchange for the Troops by sending care packages to US troops stationed overseas. Stephen's packages included some snacks, DVDs, books, and, of course, autographs. There's nothing like getting a signed photo of Stephen Colbert riding an eagle to remind yourself of what you're fighting for.
When Reddit ran their Star Trek exchange in 2013, one Reddit user was shocked to receive a package from Wesley Crusher himself, Wil Wheaton! Wil had been making the convention circuits at the time, so he sent along autographed photos from a bunch of other Star Trek actors, including George Takei, Nichelle Nichols, & Walter Koenig (plus one of himself, of course.) Wil explained that he tried to get a signature from Shatner, too, but to do so would have been a violation of the prime directive.
During 2013's Secret Santa exchange, one "lucky" participant got matched up with PBS. Not to disappoint, the PBS offices sent exactly what you'd expect them to send: the stuff they're always giving away during pledge drives (t-shirt, water bottle, tote bag, etc.) Thankfully, they also threw in some Walking Dead figures, because even PBS knows that nobody actually watches PBS.
Joe Gatto of Impractical Jokers is a generous guy. He sent his Secret Santa match a DVD of his show, an autograph, and a 4-day pass to Dragon Con in Atlanta (valued at $95). But, in true Impractical Jokers fashion, Joe's package arrived postage-due, forcing his giftee to cough up $17.83 for postage. Nice touch.
In 2011, Redditor darbyrose drew the ire of my 5-year-old self when she was randomly matched with Pee-wee Herman. The spastic man-child sent along a personally-wrapped DVD, as well as the Official Pee-wee Herman Fun Book (which retails for $60). Pee-wee was going to send one more item, but accidentally left it in the basement of the Alamo.
Arnold Schwarzenegger understands what the Internet wants, which is why during 2013's Secret Santa exchange, along with some swag from the Governor's mansion, he sent along a personally drawn portrait of his match's cat! And, just to be clear it wasn't a forgery, he included a photo of himself sketching the cat picture. The idea of Arnold creeping through his Secret Santa match's Facebook page for a good shot of her pet makes us feel all warm and fuzzy inside.
The staff of Funny or Die decided to join the Secret Santa madness in 2013, and were matched with a Redditor named Brian. Along with the customary office swag (shirt, hoodie, notebook), Brian was invited to take a personal tour of their office! He'd just better hope that Will Ferrell's landlord, Pearl, doesn't come by during his visit. I hear she's really nasty.