With the new Afro Samurai Resurrection out, I thought well since everyone loves the original I'd go and revamp it; since with the original I feel it has alot of glaring flaws and it was only my 3rd ever digital painting.
FINAL UPDATE, August 2015 - Put incoming host Trevor Noah with the outgoing Jon in the final shot...and added Gitmo! Update, January 2015 - Added Michael Che, Jordan Klepper, Trevor Noah, and Hasan Minhaj! Plus, updated image for Jessica. Update, May 2012 - Added Al Madrigal, Sarah Vowell, and Jessica Williams. Also, updated the images for Olivia and the final Jon-and-Stephen.
Update, July 2010 - Added Josh Gad and Olivia Munn.
All of Jon Stewart's correspondents on The Daily Show, in roughly chronological order.
Top row: 1999!Jon Stewart with first host Craig Kilborn; David Wain; Lizz Winstead; A. Whitney Brown; Brian Unger; Michael Blieden; Rich Brown; Beth Littleford; Frank DeCaro; Lewis Black; John Bloom; Steve Carell and TDS!Stephen Colbert; Laura Kightlinger; Paul F. Tompkins; Jeff Stilson; Mo Rocca; Paul Michael Mercurio; Vance DeGeneres; Dave Attel
Middle row: Nancy Walls; Stacy Grenrock-Woods; Andy Kindler; Eric Drysdale; David Pompeii; Miriam Tolan; Lauren Weedman; Matt Walsh; Samantha Bee with Jason Jones; Mary Birdsong; Adrianne Frost; Rachel Harris; Rob Corddry; Ed Helms; Jon Glaser; Bob Wiltfong; Nate Corddry; Dan Bakkedahl; Dave Gorman; John Hodgman; Aasif Mandvi; Demetri Martin with Schmon Schmewart
Bottom row: John Oliver; Rob Riggle; Larry Wilmore; Buck Henry; Kristen Schaal; Wyatt Cenac; Josh Gad; Olivia Munn; Al Madrigal; Sarah Vowell; Jessica Williams; Michael Che; Jordan Klepper; Trevor Noah; Hassan Minhaj; and 2015!Jon with Gitmo and incoming-host!Trevor.
Click "Download" for backgrounds (regular & widescreen), plus clean PNGs of each correspondent, and a list of all the fonts used.
This came about when I stumbled upon Doctor's Girls, and immediately thought, "Clearly, Jon Stewart needs a group portrait of his own quasi-harem."
Only later did I realize what I had gotten myself into. The Doctor has had maybe two dozen female Companions, while there have been almost sixty correspondents, and more appear all the time. (Kristen and Wyatt were added to the show while I was working on this.)