Pop! The Evolution Of Entertainment

'Pop! The Evolution of Entertainment' is a TV special that aired during the 2018 holiday season, in an alternate universe where Hillary Clinton is president. It featured guest spots from numerous celebrities and characters.

Recap
The first thing we see is a rapid-fire montage of movies, TV shows, music videos and video games set to Madeon's "Pop Culture". (Think something like this video.) We then transition to a packed stadium (i.e. the Hollywood Bowl) where the main portion of the show will be held. Jerry Seinfeld opens this portion with a monologue about many of the topics that will be covered during the evening.

Seth MacFarlane, the next speaker, chooses to speak about the silent film era and the Golden Age of Hollywood and both eras' influence on the filmmakers and content creators of today. A montage then follows of films from these periods, which itself is followed by a medley of songs from these films, performed by John Legend.

Whoopi Goldberg talks about famous cartoons such as Looney Tunes and their impact on modern society, while various cartoon characters past and present enthuse about how animation has evolved over the years. A montage where celebrities and people on the street talk about their favorite Disney movies/characters is bookended by Jessie J singing "When You Wish Upon A Star" and a Disney medley from violinist Lindsey Stirling.

Jimmy Fallon introduces a prerecorded appearance from Reggie Fils-Aime, who enthuses about Nintendo and introduces a Kate Higgins performance of "Jump Up, Super Star". A montage about the history of video games then plays, with musical accompaniment by The Piano Guys, seguing into a performance of "Your Reality" with Higgins.

Felicity Jones and Donald Glover speak about filmmaking from the blockbuster period onwards and introduce a Star Wars medley performed by the orchestra, followed by a Celine Dion performance of "Ashes" from Deadpool 2. Various stars from upcoming films then give promotions to said films in another montage, followed by a performance of at least one song from one of those films.

Conan O'Brien talks about how television has evolved over the years, and introduces a medley of TV theme songs performed by the Schuyler sisters from Hamilton: Phillipa Soo, Renée Elise Goldsberry and Jasmine Cephas Jones. A montage of the most memorable TV moments is played. Kristin Chenoweth remembers Mitzi Gaynor's famous performance of "Georgy Girl" at the Academy Awards in 1967, and performs the song.

Phillipa Soo returns to the stage to discuss the origins of Broadway theatre, and sings a short medley consisting of "Somewhere" from West Side Story and "What I Did For Love" from A Chorus Line. A montage of Tony Awards performances from various musicals over the years (in chronological order) then follows. Ben Platt then takes the stage to explain that there is a second golden age of musical theatre going on before performing "Waving Through a Window".

John Legend and Jessie J return to the stage to perform "God Only Knows". The performance is followed by a montage where celebrities and ordinary people discuss their personal heroes and the people who inspired them. Samuel L. Jackson then briefly memorializes the trailblazers in the entertainment world who are no longer with us, followed by the band Kodaline performing "All I Want".

The original VJ's of MTV discuss the impact of the channel on the music world, and introduce a "megamix" montage of videos from its first day, followed by a performance of "Video Killed the Radio Star", the first video played on MTV, in a new rendition by Fitz and the Tantrums. Jack White discusses the music that inspired him, which cues up a montage where celebrities and ordinary people discuss their favorite singers, songs and bands. The montage ends when someone mentions Queen, after which the current incarnation of Queen performs "Somebody to Love" and invites all of the night's performers back on stage to sing the closing number, "Bohemian Rhapsody".