Hollywood Cemetery represents the period of funerary art and site design between the first municipal burial ground and the late twentieth century perpetual care cemeteries with ground level, flat grave markers. Hollywood could be considered a second stage of burial ground in Madison County with its abundant funerary art and aesthetically pleasing layout and landscaping. It also reflects changing social stratification in its religious, ethnic, and economic segregation. Rather than serving the entire community, Hollywood is the cemetery of choice for Jackson's white, upper-middle-class and elite.
Hollywood stands in stark contrast to Mt. Olivet Cemetery, also in Jackson, which is the African-American graveyard established about the same time as Hollywood to provide a final resting place for the town's black community. The difference in economic status of Hollywood's deceased versus Mt. Olivet's is evident in the tombstone size and the artistic quality of the funerary art.
Salem Cemetery on Cotton Grove Road just east of the city limits exemplifies the first rural phase – a small, frontier community graveyard with no formal layout. While several of Salem's grave markers are professionally carved and aesthetically pleasing, those in Hollywood Cemetery dwarf them in size, number, and quality.
Riverside Cemetery on the south side of Jackson within one mile of the town square represents the first municipal phase – a large, integrated, municipal burial ground. Jackson's first cemetery, Riverside, contains some large and artistic tombstones; however, Hollywood Cemetery reflects Gilded Age wealth and the national trend toward designed graveyards rather than plots and streets arranged only in rectangular plans like Riverside's.
Fraternal symbols, especially those representing Woodmen of the World and Masons, are frequent. Religious symbolism is represented less often; however, some markers include crosses or "gates of heaven" while others contain religious inscriptions. A few government issued military stones mark graves of Confederate, Spanish American War, World War I and World War II veterans.
Hollywood's funerary art spans stylistic trends beginning with religious symbolism, through Victorian era idealization of nature and adoration of children, to Classic Revival and Beaux Arts. In addition, several stones exhibit the ashlar (rough cut) surfaces seen in Richardsonian Romanesque architecture of the late nineteenth century, and, like the Greek and Classical Revival influenced markers, may have its artistic origin in architecture rather than art.