2004 Playoff Prime Signatures Prime Pairings Brett Favre Daunte Culpepper Kyle Boller
Here is a great example of a card that could've at least had two awesome signatures out of three, but thanks to Duante Culpepper's fast downward spiral, and Kyle Boller being Kyle Boller, Brett Favre, one of the best QB's of all time is stuck with a guy who peaked too soon, and another guy who just never peaked. At least Culpepper had some success, but Favre deserves better than this. This was one of those examples of probably being able to pick up a Favre auto a little cheaper than say a solo certified autograph or one feature a better combination of players.
02-03 Upper Deck Playbooks Michael Jordan/Jay Williams
This is a very cool concept. It's a booklet card (kinda of predates the Triple Threads booklets) that opens and features two nice jersey swatches of Michael Jordan, the greatest player ever to play in the NBA and.....Jay Williams, #2 pick of the 02 draft. Now to be fair, this card included Jay Williams cause A)He was a spokesman for Upper Deck and B)He was supposed to be the point guard of the future for this young Chicago Bulls team, but unfortunately a motorcycle accident derailed his career permanently and we'll never really know if this card really had a chance to be something special. This set also features a dual Kobe/Jay Williams and a dual Kobe/MJ.
03-04 SPX Winning Combos LeBron James/Darko Milicic
Everyone remembers the great Darko debate and how he was chosen ahead of Carmelo Anthony, Dwyane Wade, Chris Bosh, and hell even Chris Kaman. This card looks really bad in retrospect, but at the time it was just a common pairing of the #1 and #2 picks of the 03 drafts. One just went on to become one of the greatest superstars in the league while the other....was Darko.
97-98 Topps Stadium Club Co-Signers Karl Malone/Keith Van Horn
The Co-Signers series across all sports have some very random and weird autograph combinations. I used to own a Kobe/Damon Stoudemire Co-Signers that would have made this list. Again, given the time, you were pairing an all star power forward (maybe the greatest of all time) with a supposedly future all star power forward in the #2 pick of the 97 draft Keith Van Horn. Unfortunately Van Horn became nothing but a solid journeyman and never really lived up to the hype. Karl Malone doesn't have too much certified stuff out there, it's a shame one of his auto's is paired up with Keith Van Horn.
98-99 Topps Stadium Club Co-Signers Tim Duncan/Jayson Williams
Poor Timmy, seems like when it comes to the hobby he really never gets the respect he deserves. How bout being paired with a guy tried for manslaughter in one of your few certified autographs out there? This was actually made a year after Jayson Williams made his first and only All Star team, of course injuries would end his career, but he's more famous for accidentally killing his limo driver while playing around with a loaded shotgun. Not exactly a guy who deserves to be paired with a 4 time NBA Champion and 3 times Finals MVP that's for sure.
2001 UD Minors Centennial Joe Dimaggio/Josh Hamilton Dual Jersey/Bat
Annnnnd finally the feel good redemption story. For a longgggggggggg time this card would have been considered one of the greatest slaps in the face for Joe Dimaggio. One of the most revered baseball players of all time paired up with...the biggest bust in recent memory who let drugs and alcohol ruin his career and life. How could this card exist??? Luckily for Josh Hamilton, he got his life together and did become a great baseball player not only winning the 2010 MVP but also being a main cog in leading the Texas Rangers to their first ever World Series appearance. No Josh Hamilton is not Joe Diamggio, but at least now its not unfathomable for him to share a card with the Yankee great.
Here's a question, what are you favorite head scratching dual cards in your collection???