Bloody Crossroads 2020 is a deep dive into the role that mass-appeal movies, television, videos, and music played in America’s political culture in the year of Donald Trump’s failed reelection campaign. The book also explores the impact of entertainment celebrities in communications, fundraising, and campaigning to support the election of Joe Biden. Although there existed a decades-old tradition of “liberal Hollywood,” the ascension of Donald Trump to the presidency triggered an unprecedented level of engagement by artists and performers. Within days of the 2016 election, a critical mass of entertainers, from teenagers to the last survivors of the World War II generation—blockbuster movie stars, art-film auteurs, Broadway dramatists, comedians, and musicians from the worlds of classical, country, pop, rock, R&B, and hip-hop—all seemed to have heard the tom-tom beat of resistance at the same moment and amplified a moral alternative to Trumpism. Following the opening chapters that provide context for politically outspoken entertainers since the 1940s, and the reaction of the entertainment community to the first few years of the Trump administration, the bulk of Bloody Crossroads 2020 is a detailed mosaic of the engagement of the entertainment community in the Democratic primaries, the COVID pandemic, the aftermath of the murder of George Floyd, the conviction of sexual predator Harvey Weinstein, and the 2020 general election campaign. Exhaustively researched, this volume draws from brand-new interviews with Bruce Springsteen, John Legend, Rosanne Cash, David Simon (The Wire), Adam McKay (The Big Short), Chuck D, David Corn, Eric Alterman, Ann Hornaday, Margery Tabankin (former Streisand Foundation director), Greenpeace executive director Annie Leonard, Mandy Patinkin, Kathryn Grody, Michael O’Keefe, and many more. Bloody Crossroads 2020 also explores the work of late-night comedy hosts such as Stephen Colbert and Trevor Noah; musicians, actors, and filmmakers such as Taylor Swift, Cardi B, Alyssa Milano, Mark Ruffalo, Jane Fonda, Robert De Niro, Bette Midler, Steven Spielberg, Spike Lee, Ava DuVernay, Dave Chappelle, Chris Rock, Wanda Sykes; as well as commentary from a variety of political and public interest leaders.