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Timeline
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Action Comics #1, June 1938

 
 
June 1938 - Superman makes his debut in the very first issue of Action Comics along with Lois Lane and Superman's alter ego, Clark Kent.  Superman did not appear on the cover of the second issue of Action Comics but  would rotate on the cover over the next few months with other charactes.  

 
 
 
 
                                    December, 1939 - Jimmy Olsen's first appearance.
 
 
 

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Superman #1

 
 
 
 
Summer of 1939 - Superman #1, the first comic book named after a specific character.

 
 
 
 
 
December, 1939 - Starting with Action Comics #19 Superman would appear as the cover feature for the next 49 years.

 
 
 
 
 
April, 1940 - Lex Luthor makes his first appearance in Action Comics #23.  Note:   Luthor debuts with a full head of red hair in this issue.

 
 
 
 
 
November, 1940 - Perry White, editor of the Daily Planet makes his first appearance in Superman #7.
 

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World's Best Comics #1

 
 
 
 
Spring 1941 - First issue of Worlds Best Comics starring Superman and Batman in separate features but sharing the cover.

 
 
 
 
 
 
Summer 1941 - Worlds Best Comics retitled Worlds Finest Comics with the second issue.

 
 
 
 
October/November 1941 - Superman and Batman make a brief appearance with the Justice Society of America in All-Star Comics #7.

 
 
 
 
 
July/August 1942 - Years before the Fortress of Solitude, Superman built a secret mountain retreat on a remote mountain peake in Superman #17.

 
January/February 1945 - Supermans adventures as Superboy debuted in More Fun Comics #101.

 
March/April 1949 - Superboy gets his own title, Superboy #1.

 
November/December 1949 - Krytonite first appears in the comic books in Superman #61.

 
May/June 1952 - First Superman/Batman team up in Supeman #76

 
July/August 1954 - Superman and Batman team starts a long run in Worlds Finest Comics #71.

 
September/October 1954 - Supermans Pal Jimmy Olsen #1

 
March 1955 - Krypto the Superdoy lands on Earth in Adventure Comics #210.
 
 
First Phantom Zone Appearance/Story - Adventure Comics #283
 
First Appearance of Supermans arch foes
Ultra-Humanite - Action Comics #13, June 1939
Lex Luthor - Action Comics #23, April, 1940
The Archer - Superman #13, November/December 1941
The Puzzler - Action Comics #49, June 1942
The Prankster - Action Comics #51, August 1942
The Toyman - Action Comics #64, September 1943
Mr. Mxyztplk - Superman #30, September/October 1944
Mala, Kizo and U-Ban - Superman #65, July/August 1950
Brainiac - Action Comics #242, July 1958
Bizarro - Superboy #68
Metallo - Action Comics #252, May 1959
Kryptonite Kid - Superboy #83
General Zod - Adventure Comics #283
Legion of Super-Villians - Superman #147
Jaz-Ur - Adventrue Comics #289
Superman Revenge Squad - Action Comics #286
Composite-Superman - Worlds Finest Comics #142
Parasite - Action Comics #340
Intergang - Forever People #1
Galactic Golem - Superman #248
Atomic Skull - Superman #323
Master Jailer - Superman #331
Mongul - DC Comics Presents #27
Lord Satanis - Action Comics #527
Maaldor the Darklord - DC Comics Presents #56
Blackbriar Thorn - DC Comics Presents #66

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