Hollywood with the Stars is a remarkable example of Roger Brown's mature, mid-career style. The composition features Brown's iconic architectural rendering, drawn in an "isometric style" with yellow windows highlighting the faceted forms made of black, medium gray, and light blue. The silhouette work against the windows invokes another classic motif of his style, but he modifies it by having the figures standing outside the buildings rather than inside the windows, so that they can gawk at the gigantic celebrities striding by. The red/black sky is slightly lesser known by Brown's fans in general, but was very typical of the early 1980s period in his career, not long after the death of his partner, George Veronda. The stratified, non-illusory landscape recalls the pictorial logic of pre-Renaissance traditions, a recurrent interest of Brown's, and the dual-scaled figures (where "important" people are large, and "unimportant" people are small) particularly calls back to Ancient Egyptian image craft where Pharaohs would tower over their subjects. The painting's topic however is unquestionably American, Hollywood as a culture industry and celebrities as modern legends being two fascinations of Brown's career. The gargantuan celebrity figures (among them, John Wayne, Elizabeth Taylor, James Dean, and Marilyn Monroe) speak to classic midcentury Hollywood, the movies that Brown would have seen as a child, rather than the new stars active at the time of the painting's creation. With this in mind, Brown wasn't simply creating a pop culture reference featuring hot new names and faces, but rather, purposefully proposing that these classic Hollywood icons were ascending to mythic status.

The cultural clout of Golden Age Hollywood stars was also a crucial, foundational element in the development of camp in queer counterculture of the 1960s and 1970s, Brown's own generation. Produced in secret as a commission for a Hollywood producer, the painting could appear to simply be an homage to the movie industry, but for Brown there was an equally subversive potential in the iconic figures. Each iconic Hollywood star had a carefully curated public persona, well-defined but always patently artificial, such as Marilyn Monroe's "dumb blonde" act (despite being incredibly intelligent). This character-crafting was employed, somewhat frequently, to hide a long history of LGBT performers in the industry; all of the figures present have some history of such dalliances, such as Marilyn Monroe allegedly having had one-night stands with numerous women including Joan Crawford and Elizabeth Taylor, or James Dean with co-star John Gilmore.

As a particularly cheeky gag on Brown's part, Brown included a figure vaguely resembling himself on the far right side of the painting, placing himself among the giants.

The painting was produced in secret, and remained unknown even to the Roger Brown Estate until it was uncovered by Kavi Gupta gallery shortly after they began representation. The documentation and study of the piece shed new light on Brown's expansive practice, while also prompting new questions about what other secrets may remain undiscovered.