| Issue | #39 |
| Published | May 1958 |
| Cover Price | 0.25 USD |
| Pages | 52 |
| Editing | Albert B. Feldstein |
| Characters | Alfred E. Neuman; Harry Piel; Bert Piel; Judy Garland; Bing Crosby; George Gobel; Louis Armstrong; Floyd Patterson; George Burns; Gracie Allen; Imogene Coca; Sid Caesar; Bob Hope; Ed Wynn; Steve Allen; Ed Sullivan; Jackie Gleason; Jerry Lewis; Dave Garroway; Elvis Presley; Rosemary Clooney; Jose Ferrer; Lucille Ball; Desi Arnaz; Liberace; Jayne Mansfield; Yul Brynner; Frank Sinatra |
| Genre | humor |
| Pencils | C. C. Beall Jr. (painting) |
| Inks | C. C. Beall Jr. (painting) |
| Colors | C. C. Beall Jr. (painting) |
| Letters | typeset |
| Characters | Harry Piel; Bert Piel; Judy Garland; Bing Crosby; George Gobel; Louis Armstrong; Floyd Patterson; George Burns; Gracie Allen; Imogene Coca; Sid Caesar; Bob Hope; Ed Wynn; Steve Allen; Ed Sullivan; Jackie Gleason; Jerry Lewis; Dave Garroway; Elvis Presley; Rosemary Clooney; Jose Ferrer; Lucille Ball; Desi Arnaz; Liberace; Jayne Mansfield; Yul Brynner; Frank Sinatra |
| Synopsis | List of celebrities used in the cover painting, with a black-and-white copy of the cover as an index. |
| Genre | fact |
| Pencils | C. C. Beall Jr. (painting) |
| Inks | C. C. Beall Jr. (painting) |
| Letters | typeset |
| Notes | Inside front cover. |
| Genre | fact |
| Pencils | various |
| Inks | various |
| Letters | typeset |
| Notes | Art is excerpts from this issue. |
| Synopsis | Several typewriters with specialized keys to make typing faster for various trades. |
| Genre | humor |
| Script | Frank Jacobs |
| Pencils | Bob Clarke (signed) |
| Inks | Bob Clarke (signed) |
| Letters | typeset |
| Notes | Writer credit is from "Totally MAD" CD collection. |
| Synopsis | House ad for MAD subscriptions. |
| Letters | typeset |
| Characters | Alfred E. Neuman |
| Synopsis | House ad for pinups suitable for framing. |
| Pencils | Norman Mingo (painted) |
| Inks | Norman Mingo (painted) |
| Letters | typeset |
| Synopsis | Letters of comment, mostly about issue #38. |
| Script | Albert B. Feldstein; Dennis Gormley; Steve Spiegel; Janet Bowers; Bob DeMello; Mike Conners; Jon Hartzell; Steve Ellerbroek; Nat Weber; Kenny Cohen; Johnny Schmon; Sigma Alpha Mu; I. A. Rosenthal; Bob Wade; The Boys; Gene Tortora; Everett Spencer; Robert Rickover; Steve Albers; Robert Ebenroth; Dale Anderson; Dean Martin; Michel Steinfeldt; Jay Hunt; Steve Davidson |
| Pencils | various |
| Inks | various |
| Letters | typeset |
| Notes | Art is excerpts from issue #38. |
| Characters | Alfred E. Neuman |
| Synopsis | House ad for Alfred E. Neuman jewelry designed by Astrahan of NY. |
| Pencils | Carl Klein (photo); Romeo Serry (photo touchup) |
| Inks | Carl Klein (photo); Romeo Serry (photo touchup) |
| Letters | typeset |
| Characters | Spudd Nick; Aygg Haid; Smiley; Phiz Hicks; Butch Proton; Spike Molecule; Charlie Brawn |
| Synopsis | Ideas to incorporate science lessons into various media. |
| Genre | humor |
| Pencils | Wally Wood |
| Inks | Wally Wood |
| Letters | typeset |
| Synopsis | Supposed doodles from the desks of famous people, with pop psychoanalysis. |
| Genre | humor |
| Pencils | Bob Clarke (signed) |
| Inks | Bob Clarke (signed) |
| Letters | typeset |
| Notes | Doodles from: Robert F. Wagner; Joe E. Lewis; Edward R. Murrow; Richard M. Nixon; Ed Sullivan; Pablo Picasso; Frank Costello; Alfred E. Neuman. |
| Synopsis | Discussion of the theory that the suburbs will keep moving so far out and get so crowded that eventually people will move back into the cities. |
| Genre | humor |
| Script | Dave Berg (signed) |
| Pencils | Dave Berg (signed) |
| Inks | Dave Berg (signed) |
| Letters | typeset |
| Synopsis | Illustrated version of the famous poem, with a twist ending. |
| Genre | satire |
| Script | George Pope Morris |
| Pencils | Don Martin (signed) |
| Inks | Don Martin (signed) |
| Letters | typeset |
| Characters | Romeo; Juliet |
| Synopsis | The balcony scene from Romeo & Juliet, Act II, Scene II, along with a modern beat poetry version. |
| Genre | satire |
| Script | William Shakespeare (original); Paul Laikin (adaptation) |
| Letters | typeset |
| Characters | Alfred E. Neuman; Alfred's girlfriend |
| Synopsis | New places to use subliminal advertising. |
| Genre | humor |
| Script | Paul Krassner |
| Pencils | Bob Clarke (signed) |
| Inks | Bob Clarke (signed) |
| Letters | typeset |
| Reprinted | in Mad About the Fifties (Little, Brown & Co., 1997 series) #[nn] |
| Characters | Art Barker; Bob Hope; Steve Allen; Gene Rayburn |
| Synopsis | Scenes from the following tv shows with unusual outcomes: You Asked For It; a Bob Hope special; Steve Allen Show. |
| Genre | satire |
| Script | E. Nelson Bridwell |
| Pencils | Joe Orlando |
| Inks | Joe Orlando |
| Letters | typeset |
| Notes | Writer credit is from "Totally MAD" CD collection. |
| Synopsis | Phony record album covers for opera, drawn in the style of paperback novels. |
| Genre | satire |
| Pencils | Bob Clarke (signed) |
| Inks | Bob Clarke (signed) |
| Letters | typeset |
| Synopsis | A parody of a typical high school paper. |
| Genre | satire |
| Letters | typeset |
| Synopsis | Phony U.S. postage stamps for people and events that would never be commemorated. |
| Genre | satire |
| Script | Tom Koch |
| Pencils | George Woodbridge (signed) |
| Inks | George Woodbridge (signed) |
| Letters | typeset |
| Notes | Writer credit is from "Totally MAD" CD collection. |
| Characters | Bob Elliott; Ray Goulding; Dave Sturdley; Walley Ballew; Mrs. Farber; C. C. Harkmore; Mrs. Grebinger; Hunt Brinkley; Harpley Winters; Mrs. Winters |
| Synopsis | Several roving correspondents interview people across the country during their spring cleaning. |
| Genre | satire |
| Script | Bob Elliott; Ray Goulding |
| Pencils | Mort Drucker |
| Inks | Mort Drucker |
| Letters | typeset |
| Notes | Parody of tv show; unsure of name. |
| Synopsis | Inventions over the ages that were not quite what the inventors had in mind. |
| Genre | humor |
| Script | Paul Krassner |
| Pencils | Joe Orlando |
| Inks | Joe Orlando |
| Letters | typeset |
| Notes | Writer credit is from "Totally MAD" CD collection. |
| Characters | Edwin |
| Synopsis | Instructions for three impossible, illegal, and dangerous party games. |
| Genre | humor |
| Script | Frank Jacobs |
| Pencils | Wally Wood (signed) |
| Inks | Wally Wood (signed) |
| Letters | typeset |
| Characters | Dexter Yinckley |
| Synopsis | An accountant's story of the road to failure as he changes jobs and takes the fall for the boss's embezzling. |
| Genre | humor |
| Script | Frank Jacobs [as Dexter Yinckley] |
| Pencils | George Woodbridge (signed) |
| Inks | George Woodbridge (signed) |
| Letters | typeset |
| Notes | Writer credit is from "Totally MAD" CD collection. |
| Synopsis | While dressing a mannequin, a window trimmer is assaulted. |
| Genre | humor |
| Script | Don Martin (signed) |
| Pencils | Don Martin (signed) |
| Inks | Don Martin (signed) |
| Letters | typeset |
| Synopsis | Another take on the age-old idea that people and their dogs look alike. |
| Genre | humor |
| Script | Frank Jacobs |
| Pencils | Kelly Freas |
| Inks | Kelly Freas |
| Letters | typeset |
| Notes | Writer credit is from "Totally MAD" CD collection. |
| Synopsis | A page of Cowznofski listings from a fake phone book. |
| Genre | humor |
| Letters | typeset |
| Characters | Tugboat Annie; Dietrich Dunstan Drizzle; Fenwick Overshot; Eugene Ogg; Dr. Irving Belknap |
| Synopsis | Satire of the magazine The Saturday Evening Post. |
| Genre | satire |
| Script | Tom Koch |
| Pencils | Bob Clarke (signed) |
| Inks | Bob Clarke (signed) |
| Letters | typeset |
| Notes | Writer credit is from "Totally MAD" CD collection. |
| Characters | Jerry DeFuccio |
| Synopsis | House ad for t-shirts with Alfred E. Neuman on front. Parody of both Maidenform Bra and Arrow Shirt ads. |
| Pencils | Larry Maleman (photo); Wally Wood |
| Inks | Larry Maleman (photo); Wally Wood |
| Letters | typeset |
| Notes | Model credit from Letters page of MAD #40. Inside back cover. |
| Synopsis | Movie titles paired with unlikely advertisers, such as "Noah's Ark" - Nabisco Animal Crackers. |
| Letters | typeset |
| Notes | Appear in the margins of 27 pages of the issue. |
| Synopsis | Car windshield stickers that look like official signs that would allow free parking. |
| Genre | satire |
| Pencils | Bob Clarke ? |
| Inks | Bob Clarke ? |
| Letters | typeset |
| Notes | Back cover. |