In 1997, to celebrate the 10th anniversary of Where's Waldo?, the four existing Waldo classics were re-released in special editions with Waldo's location changed in every scene and other "eye-boggling extras".

These editions gave those who already mastered the original books a chance to revisit the challenge of hunting for Waldo, as Waldo's location was moved in each scene. Additionally, the main characters not featured in the original book - namely Wenda, Woof, Wizard Whitebeard, Odlaw and the Waldo Watchers - were added (along with each character's missing item). However in the books where these secondary characters already appeared (such as the Wizard in The Great Waldo Search and the entire troupe in Where's Waldo in Hollywood), there locations were not altered - only Waldo's. Each book also included an newly added unidentified mystery character that followed Waldo through each scene and readers were asked to identify and find him or her on each page.

In the three older books, Waldo's design in the logos and other imagery was also updated to match the more current character model. As were other minor tweaks were also made - such as changing the name of "railway station" scene to "the train station" and covering up the controversial topless woman in the beach scene in Where's Waldo?.

Find Waldo Now and The Great Waldo Search were renamed Where's Waldo Now? and Where's Waldo?: The Fantastic Journey in order to incorporate the phrase "Where's Waldo" into the title.

Subsequent re-releases of these original four books - including the "mini" books, "big books", paperback editions and newer hardback releases - have all be of these updated versions. However, the notation of the books as "special edition" (and with the distinctive silver bordered covers) have since vanished. The original first edition versions of the books are currently all out of print, and have not been released since the debut of the special editions in 1997. In many of the more recent reprinting following the initial 1997 releases, the updated versions are noted only as a "second edition" along with an updated copyright in the front matter of the books.

There are no known plans for the original "first edition" versions of the books to be re-released. There are also no announced plans for the subsequent books, The Wonder Book and The Great Picture Hunt, to be updated or re-released with special edition variations.