ADVERTISEMENT
Welcome to ComicArtFans!
Return to Stolzer, Rob Return to Stolzer, Rob

Gray, Harold

Harold Gray (1894-1968) was pure genius. While I did not always agree with Gray's politics as conveyed in his brilliant Little Orphan Annie, I count the comic strip as one of my all-time favorites, right up there with Krazy Kat, Wash Tubbs, and Terry and the Pirates. Gray's Little Orphan Annie was one of the grittiest, best written, and most wonderfully drawn strips in comic strip history.

Gray was a master at using space, conveying a strong sense of presence where none was physically visible, which led to his ability to create tension. His drawing, a subtle expressionism, was the perfect vehicle for Annie and Sandy, and conveyed a sense of atmosphere unlike any other strip.

In terms of characters, Daddy Warbacks came off as somewhat one-dimensional, and a lousy parent to boot. It was Annie, Sandy, and the secondary (and sometimes tertiary) characters that really added depth to the strip.

Most of the Little Orphan Annie originals are housed at Boston University, making them pretty scarce on the marketplace. Later ones show up with some regularity, but examples from the 20s, 30s, and 40s are quite hard to find.

There are 10 Pieces of Art In This Gallery.    

This Room is Ordered By The Owner's Preference.

Harold Gray - 1928 Little Orphan Annie Comic Art
+

Harold Gray - 1928 Little Orphan Annie

Art Details

Artist: Harold Gray (All)
Media Type: Pen and Ink
Art Type: Comic Strip
For Sale Status: NFS
Views 4110
Comments: 2
Added to Site: 4/11/2006

About the Owner

Rob Stolzer Paid Member
Member Since: September 2004

Harold Gray - 1928 Little Orphan Annie
Artist: Harold Gray (All)
4110 Views, 2 Comments

Harold Gray - 1935 Little Orphan Annie Daily - Eli Eon Story Arc Comic Art
+

Harold Gray - 1935 Little Orphan Annie Daily - Eli Eon Story Arc

Art Details

Artist: Harold Gray (All)
Media Type: Pen and Ink
Art Type: Comic Strip
For Sale Status: NFS
Views 228
Comments: 7
Added to Site: 4/16/2024

About the Owner

Rob Stolzer Paid Member
Member Since: September 2004

Harold Gray - 1935 Little Orphan Annie Daily - Eli Eon Story Arc
Artist: Harold Gray (All)
228 Views, 7 Comments

Harold Gray - Original Panels from a 1935 Little Orphan Annie Sunday Page Comic Art
+

Harold Gray - Original Panels from a 1935 Little Orphan Annie Sunday Page

Art Details

Artist: Harold Gray (All)
Media Type: Pen and Ink
Art Type: Comic Strip
For Sale Status: NFS
Views 2191
Comments: 2
Added to Site: 12/11/2019

About the Owner

Rob Stolzer Paid Member
Member Since: September 2004

Harold Gray - Original Panels from a 1935 Little Orphan Annie Sunday Page
Artist: Harold Gray (All)
2191 Views, 2 Comments

Harold Gray - 1936 Little Orphan Annie Daily - Jack Boot Story Comic Art
+

Harold Gray - 1936 Little Orphan Annie Daily - Jack Boot Story

Art Details

Artist: Harold Gray (All)
Media Type: Pen and Ink
Art Type: Comic Strip
For Sale Status: NFS
Views 8321
Comments: 1
Added to Site: 4/12/2006

About the Owner

Rob Stolzer Paid Member
Member Since: September 2004

Harold Gray - 1936 Little Orphan Annie Daily - Jack Boot Story
Artist: Harold Gray (All)
8321 Views, 1 Comment

Harold Gray - Little Joe Sunday Page - 1940 Comic Art
+

Harold Gray - Little Joe Sunday Page - 1940

Art Details

Artist: Harold Gray (All)
Media Type: Pen and Ink
Art Type: Comic Strip
For Sale Status: NFS
Views 228
Comments: 0
Added to Site: 5/26/2023

About the Owner

Rob Stolzer Paid Member
Member Since: September 2004

Harold Gray - Little Joe Sunday Page - 1940
Artist: Harold Gray (All)
228 Views

Harold Gray - Little Joe Sunday Page - 1940 Comic Art
+

Harold Gray - Little Joe Sunday Page - 1940

Art Details

Artist: Harold Gray (All)
Media Type: Pen and Ink
Art Type: Comic Strip
For Sale Status: NFS
Views 1666
Comments: 0
Added to Site: 3/21/2019

About the Owner

Rob Stolzer Paid Member
Member Since: September 2004

Harold Gray - Little Joe Sunday Page - 1940
Artist: Harold Gray (All)
1666 Views

Harold Gray - Huge 1944 Little Orphan Annie & Sandy Specialty Drawing Comic Art
+

Harold Gray - Huge 1944 Little Orphan Annie & Sandy Specialty Drawing

Art Details

Artist: Harold Gray (All)
Media Type: Pen and Ink
Art Type: Comic Strip
For Sale Status: NFS
Views 1679
Comments: 3
Added to Site: 12/7/2020

About the Owner

Rob Stolzer Paid Member
Member Since: September 2004

Harold Gray - Huge 1944 Little Orphan Annie & Sandy Specialty Drawing
Artist: Harold Gray (All)
1679 Views, 3 Comments

Harold Gray - 1956 Little Orphan Annie Daily - Cops, Cops, Cops Comic Art
+

Harold Gray - 1956 Little Orphan Annie Daily - Cops, Cops, Cops

Art Details

Artist: Harold Gray (All)
Media Type: Pen and Ink
Art Type: Comic Strip
For Sale Status: NFS
Views 1126
Comments: 1
Added to Site: 11/13/2018

About the Owner

Rob Stolzer Paid Member
Member Since: September 2004

Harold Gray - 1956 Little Orphan Annie Daily - Cops, Cops, Cops
Artist: Harold Gray (All)
1126 Views, 1 Comment

Harold Gray - 1968 Little Orphan Annie  Comic Art
+

Harold Gray - 1968 Little Orphan Annie

Art Details

Artist: Harold Gray (All)
Media Type: Pen and Ink
Art Type: Comic Strip
For Sale Status: NFS
Views 1978
Comments: 2
Added to Site: 7/21/2010

About the Owner

Rob Stolzer Paid Member
Member Since: September 2004

Harold Gray - 1968 Little Orphan Annie
Artist: Harold Gray (All)
1978 Views, 2 Comments

Wall of Little Orphan Annie Dailies Comic Art
+

Wall of Little Orphan Annie Dailies

Art Details

Artist: Harold Gray (All)
Media Type: Pen and Ink
Art Type: Comic Strip
For Sale Status: NFS
Views 942
Comments: 4
Added to Site: 4/9/2012

About the Owner

Rob Stolzer Paid Member
Member Since: September 2004

Wall of Little Orphan Annie Dailies
Artist: Harold Gray (All)
942 Views, 4 Comments

There are 10 Pieces of Art In This Gallery.    

This Room is Ordered By The Owner's Preference.

 

Search This Gallery


Art By Type (within this Gallery)

 

Art By Popularity (within this Gallery)

 

Art By Year (within this Gallery)

Art By Artist (within this Gallery)

 

About the Owner

Rob Stolzer
Premium Gallery Owner
Joined: September 2004
Last Login: January 2026
Ebay Id: robart
Website: https://freeassociationfunnies.com/
Country: UNITED STATES
On CAF:

Rob's Classifieds
Artworks Commented On
Liked Art
Site Activity on CAF

Read More About RobStolzer

Contact the Owner

Use can use a contact form to send an email to this gallery owner,
but, you must be logged in to use this feature.

Latest Updates

All

ComicLINK.Com Auctions

1/24/2026 9:11:00 AM

Foggy Bottom

1/24/2026 8:41:00 AM

paul skidmore

1/24/2026 8:12:00 AM

CArt Gallery Rome

1/24/2026 8:01:00 AM

Dean Juliette

1/24/2026 7:22:00 AM

 

R Berman

1/24/2026 7:18:00 AM

Patrick Le Cerf

1/24/2026 7:15:00 AM

ENRIQUE ALONSO

1/24/2026 7:13:00 AM

Marzio Frei

1/24/2026 7:12:00 AM

Andy Brown

1/24/2026 6:35:00 AM




eBay Auctions ADVERTISEMENT

Baraldi original illustration 13x17cm approx

Heritage Auctions

Don Perlin, Ian Akin, and Brian Garvey The Transfo

ComicLink Auctions

TODD MCFARLANE AMAZING SPIDER-MAN #309 COVER (1989, CLASSIC MCSPIDEY POSE, MJ & 1ST STYX AND STONE)

Comic Connect Auctions

Tony Moore - Walking Dead #1, Page 7

Hakes Auctions

HAWKMAN VOL. 3 #27 COMIC BOOK COVER ORIGINAL ART BY RON LIM.












Subscribe to the YouTube Channel.. FREE!




Featured Art Rep
Japan Comic Art Expo Logo Japan Comic Art Expo
8 Repped Artists
0 Accepting Commissions
Oshiyama
Benjamin
Omori
Takaiwa

 

Commission an Artist


For Sale Updates

Classified Updates

ComicLINK.Com Auctions

1/24/2026 9:11:00 AM

Foggy Bottom

1/24/2026 8:41:00 AM

CArt Gallery Rome

1/24/2026 8:01:00 AM

Patrick Le Cerf

1/24/2026 7:15:00 AM

ENRIQUE ALONSO

1/24/2026 7:13:00 AM

Robert Hughes

1/23/2026 7:28:00 PM

Dealer Updates

RomitaMan Original Art

1/24/2026 5:27:00 AM

Coollines Artwork

1/23/2026 9:53:00 PM

Koch Comic Art

1/23/2026 7:20:00 PM

Anthony's Comicbook Art

1/23/2026 4:51:00 PM

ComiConArt

1/23/2026 3:57:00 PM

Catskill Comics

1/23/2026 2:15:00 PM





Become a Premium CAF Gallery Owner & you'll be supporting CAF and also gain access to many services and features not available to standard members.

  • Sell Artwork in the CAF Classifieds
  • Daily Email Alerts based on your own Searches
  • Follow Other Gallery Owners
  • 6 Months Market Data Access
  • Larger Image Uploads ... and Much More!