That Long Jakes

Lesson Plan


Students will compare and contrast the Long Jakes painting to the whimsical illustration for the poem “Backward Bill” by Shel Silverstein. They will discuss similarities and differences in the main character’s expression, position, and other visual elements and write a rhyming poem for Long Jakes similar to “Backward Bill.”

Intended Age Group

Elementary (grades K-5)

Length of Lesson

One 55 minute lesson

Standards Area

Language Arts


Students will be able to:

  • compare and contrast two pieces of visual art;
  • arrange their observations in an organized way; and
  • plan and draft a simple rhyming poem based on a work of art.


  1. If you do not have Internet access, hand out printed copies of “Backward Bill” to students. Be sure to photocopy Silverstein’s illustration. If you do have Internet access in your classroom and are hooked up to a projector, go to Shel Silverstein YouTube channel to view the "Backward Bill" animation. You may choose to read the rest of “Backward Bill” to the class independently.
  2. Discuss how Silverstein’s illustration of Backward Bill fits with the tone of poem. Encourage students to use descriptive words in the discussion, such as goofy, corny, funny, and silly.
  3. Draw a SIMILARITIES and DIFFERENCES diagram on the board using the example provided in "Materials".
  4. Display Long Jakes, “The Rocky Mountain Man” for the students to see. Discuss the similarities between Long Jakes and the illustration of Backward Bill and write them on the board (i.e. both men, both mounted on horses, both wearing hats).
  5. Now look for differences such as facial expression, posture, landscape, horse. (i.e. Long Jakes’s serious expression, Backward Bill’s goofy face; Long Jakes is in the mountains, Backward Bill is not surrounded by any landscape). Write these differences on the board.
  6. After finding at least 4–5 differences, ask students to compose a simple rhyming poem based on items listed in the Long Jakes DIFFERENCES column. With younger students, use the poem template for That Long Jakes. Have older students compose their own poems individually. Emphasize that organized notes help create an outline for a poem. A good place to start might be one rhyming couplet per DIFFERENCE listed.


  • Computer with Internet access, speakers, and projection set up to show a video animation of "Backward Bill"


  • Copies of the illustration for Shel Silverstein’s poem “Backward Bill” found in his book A Light in the Attic (HarperCollins, 1981)



CO Standards

  • Visual Arts
    • Observe and Learn to Comprehend
    • Relate and Connect to Transfer
  • Language Arts
    • Oral Expression and Listening
    • Research and Reasoning
    • Writing and Composition
    • Reading for All Purposes

21st Century Skills

  • Collaboration
  • Critical Thinking & Reasoning
  • Information Literacy
  • Invention
  • Self-Direction

About the Art

Long Jakes

Long Jakes, "The Rocky Mountain Man"


Charles Deas

Who Made It?

Born in Philadelphia, Charles Deas [DAYS] enjoyed an education based in the classics (which included art) and he aspired to a military life. He was denied admission to West Point Military Academy, after which he began studying art. Deas traveled west in 1840 to visit his brother at Fort Crawford in the Wisconsin Territory and moved around that region for the next year or so, painting scenes of the frontier, Indians, and military portraits. He settled in St. Louis, the gateway to the West, where he set up a studio and made it his home base for expeditions. Deas immersed himself so completely in the frontier lifestyle that he earned the nickname “Rocky Mountains.” He dressed like a trapper, according to a soldier he traveled with, in “a broad white hat—a loose dress, and sundry traps and truck hanging about his saddle.” That description doesn’t sound far off from what we see in this painting, and some think that Deas personally identified with the Long Jakes figure.

Deas’s art was exhibited in St. Louis as well as New York and Philadelphia. He enjoyed critical acclaim and lived to see the immense popularity of Long Jakes. He was a prolific artist, even though he only had a 12-year painting career. However, most of his paintings have either been lost or are not recognized as his, and only 30-40 are known today. Deas died in 1867 in a New York mental institution.

What Inspired It?

Long Jakes documents America’s first frontier hero, the fur trapper. The fur trade in the American West flourished in the 1830s and was one of the most financially successful industries in America during the first half of the 1800s. The image of the trapper was that of a fiercely independent traveler who led a solitary life. Trappers worked throughout the Rocky Mountains to gather beaver fur, a major commodity (beaver hats were very popular). Trappers were often seen as rebels living outside the limits of society, but more often they were viewed with a sort of heroism, the ideal of the independent American spirit.

Using painting conventions usually reserved for kings and generals, Deas placed this motley American hero on his horse, top and center, elevated over a vast landscape. Critics discerned refinement and sensitivity behind his weather-beaten face. Long Jakes is turned in his saddle, looking with concern at something we can’t see. Clearly, the West was filled with danger and adventure at every turn.

When Long Jakes was exhibited, the heyday of the trapper was over, so it seems the picture summed up the spirit of an idealized time in its tribute to the courage and lifestyle of these men. This painting set the ongoing iconography for how to represent a trapper.


Evidence of the Outdoor Life
Evidence of the Outdoor Life

Long Jakes’s beard, long hair, and sunburned face are all signs of life in the harsh outdoors. Also note his blue-veined, chapped hands.


This mountain man’s garb was assembled based on availability and functionality. His long red hunting shirt is made of trade cloth. A broadbrimmed hat would guard his eyes from sun glare, hail, and sleet. He wears leggings with quillwork decoration and moccasins fitted with spurs.

Trapper Gear
Trapper Gear

The rifle, bedroll, powder horn, knife, and rope are all items that were associated with trappers. His saddle has been identified as a Mexican one.

Red Nose
Red Nose

At the time, a red nose was a well-recognized sign of someone who drank excessively, and it made the figure somewhat humorous to its 19th century audience.

Bulging Eye
Bulging Eye

Whatever is happening off to the left has alarmed the horse. Its bulging eye and startled gait suggest fear.


A brand is barely visible on the horse’s hind leg. It was previously thought to be the letters JS but is now thought to be the letters US. We know Deas rode a horse that formerly belonged to the government; perhaps the same is true of Long Jakes’s horse.

View of the Rockies
View of the Rockies

The mountains had a symbolic association with trappers, so they’re almost like another trapper accessory. This is a very early use of the Rockies as a backdrop, and it’s unclear whether it’s based on an eyewitness experience.

Funding for lesson plans provided by a grant from the Morgridge Family Foundation. Additional funding provided by the William Randolph Hearst Endowment for Education Programs, and Xcel Energy Foundation. We thank our colleagues at the University of Denver Morgridge College of Education.