The eight joint portraits of Sitting Bull and "Buffalo Bill" Cody were part of a commission for 47 photographs, which were printed and sold as cabinet cards during the tour.

The depiction of his relationship with Cody in Sitting Bull and Buffalo Bill has been analyzed and criticized by scholars as a representation of the dynamics of settler colonialism in the United States.

[1] During the Great Sioux War, the showman, soldier and hunter William F. Cody, better known as Buffalo Bill, was chief of scouts of the 5th Cavalry Regiment.

[7] Cody's dramatization of the incident furthered his career as a showman,[7] eventually becoming part of Buffalo Bill's Wild West, the show which he created in 1883.

[4] In 1881, after a four-year exile in Canada which was marked by insufficient food and resources, Sitting Bull returned to the border and surrendered to United States officials.

[9] After relentless pressure from Cody and his manager, John Burke, Lamar eventually relented and agreed for Sitting Bull to appear in the show's parade and in the arena, although not as a performer in the reenactments.

[note 4][10] In Montreal, where the Wild West arrived on 10 August and settled for a week (in the neighbourhood of Pointe-Saint-Charles),[13] Sitting Bull was treated as an important visitor; he was presented to local Iroquois chiefs and invited to a steamboat ride on the St. Lawrence River.

[10] While in Montreal, the Wild West commissioned a series of new souvenir photographs from the studio William Notman & Son, possibly due to their previous stock having been exhausted.

[16] According to the art historian Jana L. Bara, Notman likely photographed Sitting Bull and Cody himself: "He was known to give important sitters his personal attention, as it was in his interest to ensure the proper treatment of stars of such calibre and to add them to his ever-growing list of celebrities.

[12][4] While its title on cabinet cards read Sitting Bull and Buffalo Bill,[20] it was frequently published with the caption "Enemies in '76, Friends in '85", in reference to its subjects' opposing allegiances during the Great Sioux War.

[16] The dual portraits of Sitting Bull and Cody are set up in front of a painted backdrop representing northeast woodland, populated by birch trees.

[note 7][12] Sitting Bull's head is adorned with a floor-length eagle-feather headdress,[10] and he wears a fringed leather shirt and loose, dark trousers.

[23] He referred to Buffalo Bill, who "gladly strikes a pose, exaggerating it just a tad", in contrast to Sitting Bull's "motionless stance" and his eyes, which "find a way to signal that they are not looking where they are being told to".

[23] Dudemaine interpreted Buffalo Bill as "substituting Custer", with his similar moustache and goatee, and wrote that Sitting Bull portrays himself as "a proud fighter capable of valiantly resisting the assaults of the conqueror".

[23] On the other hand, the American studies scholar Joy Kasson wrote that the "balance of power seems to tip toward Cody", who "seems active and masterful, pointing the way to the acquiescent warrior".

[12] On the same subject, Joy Kasson wrote that "the 'friendship' offered in this photograph —and in Wild West performances— honored American Indian dignity only at the expense of surrender to white dominance and control.

[23] The author Deanne Stillman wrote that it was "a hallmark of the Wild West",[16] while the historian Jean-François Nadeau [fr] said that it was "the most famous photograph of the Western legend".