Chadwick Boseman
Karier > 1993–2007: Theater, Deep Azure, dan televisi

Boseman tinggal di Brooklyn, Kota New York, pada permulaan kariernya. Pada tahun 2000, ia dinobatkan sebagai Drama League Directing Fellow. Ia menyutradarai produksi termasuk The Colored Museum karya George C. Wolfe (George kemudian menyutradarai Boseman dalam peran terakhirnya) dan pementasan Dutchman karya Amiri Baraka. Ia bekerja sebagai instruktur drama di Schomburg Junior Scholars Program, yang bertempat di Schomburg Center for Research in Black Culture di Harlem antara 2002 dan 2009. Dia menjadi terkenal sebagai penulis naskah dan aktor panggung pada tahun 2002, tampil dalam beberapa sandiwara dan memenangkan penghargaan AUDELCO pada tahun 2002 atas perannya dalam Urban Transitions karya Ron Milner. Sebagai anggota National Shakespeare Company of New York, ia memerankan Romeo di Romeo and Juliet dan Malcolm di Macbeth. Dia menulis dan menyutradarai pementasan teater saat menjadi bagian dari gerakan Hip-hop theater. Karyanya termasuk Rhyme Deferred (ditulis bersama teman kuliah di Howard University Kamilah Forbes), di mana dia juga tampil, dan Hieroglyphic Graffiti. Rhyme Deferred dikomisi untuk tur nasional, dan termasuk dalam antologi The Fire This Time. Sedangkan Hieroglyphic Graffiti diproduksi di berbagai lokasi, termasuk National Black Theatre Festival di 2001. Menggabungkan budaya Afrika-Amerika modern dan dewa-dewa Mesir, ceritanya berlatar di Washington, D.C., dan dipilih oleh New York Hip-Hop Theatre Festival serta program summer stock theatre milik Tennessee State University di 2002. Pementasan teater itu pun termasuk dalam peluncuran produksi Kuntu Repertory Theatre di musim 2002–03. Pada Hip-Hop Theatre Festival 2002, Boseman menampilkan pertunjukkan tunggal "Red Clay and Carved Concrete".
In 2003, Boseman was cast in his first television role, an episode of Third Watch, and began playing Reggie Montgomery in the daytime soap opera All My Children. He was fired from All My Children after voicing concerns to producers about racist stereotypes in the script; the role was subsequently re-cast, with Boseman's future Black Panther co-star Michael B. Jordan taking the part. Boseman had wanted to work around the stereotypes of the character, feeling that being in a soap opera would give him more room for improvisation as the writers often do not initially plan a full story; his (then-future) agent said that when Boseman was given the second script and learned that his character's parents were a drug addict and an absent father, Boseman confronted the creators. He reflected on the experience in his 2018 commencement address to Howard University, saying that it "seemed to be wrapped up in assumptions about us as black folks [and he] would have to make something out of nothing." His other early television work included episodes of the series Law & Order, Cold Case, CSI: NY, and ER.
His best-known play, Deep Azure, was commissioned in 2004 by the Congo Square Theatre Company in Chicago. It was nominated for a 2006 Jeff Award for Best New Work. Boseman said at the time that Deep Azure was "a fusion and progression of [his] previous plays", which he did not feel fit wholly in the Hip Hop theater genre. The play – about police brutality, a daring subject in 2004, and largely delivered in rhyme – was workshopped at the Apollo Theater in New York. Critic Chris Jones highly praised the work. In 2008, Boseman turned Deep Azure into a screenplay. Michael Greene, who would become his agent, picked it up and contacted Boseman when Tessa Thompson and Omari Hardwick expressed an interest in playing the lead roles, prompting Boseman's move to Los Angeles. He also directed, wrote, and produced the short film Blood Over a Broken Pawn in 2007, which was honored at the 2008 Hollywood Black Film Festival.