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Sell or Auction Your Charlie Chaplin Signed Self Caricature for up to $2,500 or More at Nate D. Sanders Auctions

ByNate D Sanders May 4, 2023December 1, 2023

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Do you have a high-value item that you would like to get the maximum price possible? If so, please call us at (310) 440-2982 or use the form below. A representative of Nate D. Sanders Auctions will contact you concerning your items.

Attach up to 4 pictures in gif, jpg or png format not to exceed 4Mb.

There are two methods to select your images after you clicking “Choose Files”:

While holding the Shift Key down, select the first image and the last image. All images between will be highlighted.

While holding the CTrl Key down, select each image one click at a time. Only the selected images will be chosen. Then click “Open” and the selected files will be included in the form.

You can also email us at [email protected]

Consign With Us

Do you have a high-value item that you would like to get the maximum price possible? If so, please call us at (310) 440-2982 or use the form below. A representative of Nate D. Sanders Auctions will contact you concerning your items.

Attach up to 4 pictures in gif, jpg or png format not to exceed 4Mb.

There are two methods to select your images after you clicking “Choose Files”:

While holding the Shift Key down, select the first image and the last image. All images between will be highlighted.

While holding the CTrl Key down, select each image one click at a time. Only the selected images will be chosen. Then click “Open” and the selected files will be included in the form.

You can also email us at [email protected]

FREE VALUATION. To buy, auction, sell or consign your Charlie Chaplin signed self caricature that is for sale, please email your description and photos to [email protected] of Nate D. Sanders Auctions (http://www.NateDSanders.com).

Free Appraisal, Auction or Sell Your Charlie Chaplin Signed Self Caricature

We at Nate D. Sanders Auctions sold some Charlie Chaplin signed self caricatures. Please see details below:

Nice Charlie Chaplin Signature & Sketch of His Iconic “Tramp” Character from an Autograph Book

Excellent Charlie Chaplin signature and sketch of his most famous silent film character, “The Tramp.” Here, Chaplin signed his name in an autograph book in blue ink: “To Daphne / Best Wishes / Charlie Chaplin” with a nice 2″ drawing by Chaplin of The Tramp. Signed page measures 6.25″ x 4″. Chaplin signature page is in very good condition. Sold for $2,500.

Charlie Chaplin signed self caricature
Click image to enlarge.

Charlie Chaplin Autograph & Self-Portrait Sketch of Himself as The Tramp — With PSA/DNA COA

Autograph book containing the autograph of Charlie Chaplin, who also draws a whimsical self-portrait of himself as The Tramp. Chaplin writes next to the caricature in black fountain pen, “To Peter / Lots of love / Charlie Chaplin”. Autograph book includes several more signatures by Golden Age Hollywood actors, including Douglas Fairbanks, Jr. and his wife. Autographs were obtained in the early 1940s, with book belonging to a man named Peter Gifford. Album measures 5.675″ x 3.75″. Vertical crease to front cover of book, pages remain in very good to near fine condition. With PSA/DNA COA for Chaplin’s signature. Sold for $1,200.

Charlie Chaplin signed self caricature
Click image to enlarge.
PSA/ DNA COA. Click image to enlarge.

We also sold the following Charlie Chaplin signed items:

Charlie Chaplin Signed Photograph as the Tramp — With JSA COA

Rare photograph signed by silent movie star Charlie Chaplin. Iconic and beloved actor signs ”Faithfully / Charlie Chaplin” to image of himself as the memorable Tramp. Black and white photograph measures 5” x 7”. Light toning and creasing, not affecting signature, which remains bold. Very good plus condition. With JSA COA. Sold for $3,125.

Charlie Chaplin signed self caricature
Click image to enlarge.
PSA/ DNA COA. Click image to enlarge.

Charlie Chaplin Signed Photo as “The Tramp”

Charlie Chaplin signed photo in his most famous character as “The Tramp”. Semi-matte photo measures 5″ x 7″, boldly signed in black ink, “Faithfully / Chas Chaplin”. Light wear, overall very good plus condition. Sold for $2,000.

Charlie Chaplin signed self caricature
Click image to enlarge.

Charlie Chaplin Signed 11″ x 14″ Photo — Gorgeous Matte Photo Signed in Bold Blue Ink by Chaplin

Charlie Chaplin signed 11″ x 14″ silver gelatin photo, a stunning image taken in 1921 by Strauss Peyton Studios. Matte photo is signed by Chaplin in blue fountain pen, “To Lottie – With my very best wishes for a happy New Years / Sincerely yours / Charlie Chaplin”. Discreet ink spots near Chaplin’s buttons, and slight wear to margins, not affecting image. Overall very good to near fine condition. Sold for $1,600.

Charlie Chaplin signed self caricature
Click image to enlarge.

Scarce 1916 Charlie Chaplin Typed Letter Signed — On Letterhead of His Short Lived Music Publishing Company

Charlie Chaplin signed 11″ x 14″ silver gelatin photo, a stunning image taken in 1921 by Strauss Peyton Studios. Matte photo is signed by Chaplin in blue fountain pen, “To Lottie – With my very best wishes for a happy New Years / Sincerely yours / Charlie Chaplin”. Discreet ink spots near Chaplin’s buttons, and slight wear to margins, not affecting image. Overall very good to near fine condition. Sold for 1,562.

Charlie Chaplin signed self caricature
Click image to enlarge.

Charlie Chaplin Original Divorce Documents Signed With His Full Legal Name — Bitter Follow-Up to his Sensational 1927 Divorce With Actress Lita Grey: “I am not forgetting the fact that Mr. Chaplin has done very well with his own investments”

Riveting collection of over 25 legal documents regarding Charlie Chaplin’s divorce from Lita Grey, including Chaplin’s 1935 Statement of Income, numerous letters by Grey and the cornerstone of the lot, a “Declaration of Trust” for the couple’s two children, twice signed by Chaplin, “Charles Spencer Chaplin” and “Charles Chaplin” establishing a $100,000 trust fund for each of their two children. The lot overall is a fascinating page-turner, with Grey staking her claim to Chaplin’s fortune through letters such as this one dated 22 April 1935: “leave no stone unturned as far as the delving into records is concerned—- as well as the study of the psychological phases of the case. My dealings with Mr. Chaplin up to the present time have been anything but pleasant. I think that even he, at this time, would agree— that I am right in expecting the trust agreement to read very much in favor of the children. I am not, at this time, expecting him to play me a dirty trick.” Lot also includes numerous legal and financial documents examining Chaplin’s personal finances, stock portfolio and property investments. In 1924, Chaplin secretly married the 16-year old Grey in Mexico, but they divorced three years later on grounds that he was having affairs with several other women. The 1927 Chaplin-Grey divorce proceedings were a media sensation with the divorce settlements, the largest ever. Chaplin was forced to pay a then-unheard of $600,000 lump sum to Grey and establish $100,000 trust funds for each of their two children. Lot is in very good condition with the 16pp., 8.5″ x 13″ trust agreement in near fine condition; signatures are bold and clear and paper has been nicely preserved. An extraordinary archive of Hollywood memorabilia. Sold for $1,484.

Charlie Chaplin signed self caricature
Click image to enlarge.

Charlie Chaplin Signed Autobiography to His Friend, the Photographer Alfred Eisenstaedt

Charlie Chaplin signed copy of ”My Autobiography”, inscribed to famed photographer Alfred Eisenstaedt. London: The Bodley Head, 1964 third impression of the first edition. Upon the dedication page Chaplin addresses Eisenstaedt by ”Eizie”, slightly misspelling his nickname Eisie: ”To Eizie – Hoping you will enjoy this book / Charlie Chaplin / Feb 1966”. Measures 5.75” x 8.75”. Housed in original unclipped dust jacket, which has a small amount of chipping, overall very good condition. Book is slightly cocked with separation starting at front joint, also in very good condition. From Alfred Eisenstaedt’s estate. Sold for $750.

Click image to enlarge.

FREE VALUATION. To buy, auction, sell or consign your Charlie Chaplin signed self caricature that is for sale, please email your description and photos to [email protected] of Nate D. Sanders Auctions (http://www.NateDSanders.com).

We offer the following services for your Charlie Chaplin signed self caricature:

  • Appraise Charlie Chaplin signed self caricature.
  • Auction Charlie Chaplin signed self caricature.
  • Consign Charlie Chaplin signed self caricature.
  • Estimate Charlie Chaplin signed self caricature.
  • Sell Charlie Chaplin signed self caricature.

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© 2026 Hollywood Memorabilia, Fine Autographs, & Consignments Blog

Consign With Us

Do you have a high-value item that you would like to get the maximum price possible? If so, please call us at (310) 440-2982 or use the form below. A representative of Nate D. Sanders Auctions will contact you concerning your items.

Attach up to 4 pictures in gif, jpg or png format not to exceed 4Mb.

There are two methods to select your images after you clicking “Choose Files”:

While holding the Shift Key down, select the first image and the last image. All images between will be highlighted.

While holding the CTrl Key down, select each image one click at a time. Only the selected images will be chosen. Then click “Open” and the selected files will be included in the form.

You can also email us at [email protected]

Consign With Us

Do you have a high-value item that you would like to get the maximum price possible? If so, please call us at (310) 440-2982 or use the form below. A representative of Nate D. Sanders Auctions will contact you concerning your items.

Attach up to 4 pictures in gif, jpg or png format not to exceed 4Mb.

There are two methods to select your images after you clicking “Choose Files”:

While holding the Shift Key down, select the first image and the last image. All images between will be highlighted.

While holding the CTrl Key down, select each image one click at a time. Only the selected images will be chosen. Then click “Open” and the selected files will be included in the form.

You can also email us at [email protected]

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