New York, early 1960s. Against the backdrop of a vibrant music scene and tumultuous cultural upheaval, an enigmatic 19-year-old from Minnesota arrives in the West Village with his guitar and revolutionary talent, destined to change the course of American music.
| Bob Dylan | Timothée Chalamet |
| Pete Seeger | Edward Norton |
| Sylvie Russo | Elle Fanning |
| Joan Baez | Monica Barbaro |
| Woody Guthrie | Scoot McNairy |
| Albert Grossman | Dan Fogler |
| Johnny Cash | Boyd Holbrook |
| Bob Neuwirth | Will Harrison |
| Dave Van Ronk | Joe Tippett |
| Toshi Seeger | Eriko Hatsune |
| Frank (Lawyer) | Peter Gray Lewis |
| Federal Judge | Peter Gerety |
| Federal Court Clerk | Lenny Grossman |
| Cab Driver | David Wenzel |
| Danny Seeger | Riley Hashimoto |
| Tinya Seeger | Eloise Peyrot |
| Mika Seeger | Maya Feldman |
| Tito (Gerdes Stage Manager) | Reza Salazar |
| Gerdes M.C. | James Austin Johnson |
| John Hammond | David Alan Basche |
| Brownie McGhee (Blues Musician) | Joshua Henry |
| Alan Lomax | Norbert Leo Butz |
| Gena Russo | Alaina Surgener |
| Civil Rights Speaker | Martin Fisher |
| Mailman | Craig Geraghty |
| Orderly | Michael Everett Johnson |
| Young Musician at Party | Jater Webb |
| Jimmy Dean | Andy Talen |
| Man On Payphone | Andrew Kober |
| Tom Wilson | Eric Berryman |
| CBS Receptionist | Molly Jobe |
| Girl #1 (D.C. Hotel) | Sophie Hart |
| Girl #2 (D.C. Hotel) | Taylor Valentine Lupini |
| Harold Levanthal | P.J. Byrne |
| Peter Yarrow | Nick Pupo |
| Street Vendor | Brendan Burke |
| Becka | Laura Kariuki |
| Tilda | Zoe Zien |
| Party Guest #1 | Kevyn Morrow |
| Party Guest #2 | Andy Grotelueschen |
| Party Guest #3 | Jonathan Spivey |
| Party Guest #4 | Cilda Shaur |
| Party Guest #5 | Clark Carmichael |
| Woman at McAnn's | Taylor Goodwyn |
| Sylvie's New Boyfriend | Arthur Langlie |
| Theodore Bikel | Michael Chernus |
| Roy Halee (Engineer) | Jordan Goodsell |
| Mike Bloomfield | Eli Brown |
| Jesse Moffette | Big Bill Morganfield |
| Jonah (TV Floor Director) | Liam Craig |
| Al Kooper | Charlie Tahan |
| Harvey Brooks (Columbia Records) | Ian Kagey |
| Newport Cab Driver | Dave Maulbeck |
| Spacey Girl | Lorin Doctor |
| Kid in Crowd | Aidan Close |
| Girl in Crowd | Irina Chelidze |
| Newport Festival Fan #1 | Jenna Veal |
| Newport Festival Fan #2 | Joshua Flinchbaugh |
| Newport Festival Fan #3 | Cameron G. Quevedo |
| Newport Festival Fan #4 | Alexis Felix |
| Joe Boyd (Sound Engineer) | Will Price |
| Angry Fan | Sunny Vinsavich |
| Maria Muldaur | Kayli Carter |
| Sony Terry (Blues Musician) | Steve Bell |
| Marshall Grant (Tennessee 3) | Malcolm Gold |
| Luther Perkins (Tennessee 3) | Patrick Phalen |
| W.S. Holland (Tennessee 3) | Douglas Marriner |
| Barry Goldberg (Newport Band '65) | Justin Levine |
| Sam Lay (Newport Band '65) | Mark Whitfield, Jr. |
| Jerome Arnold (Newport Band '65) | Joshua Crumbley |
| Kenny Rankin (Columbia Records) | Felix Lemerle |
| Bruce Langhorne (Columbia Records) | Malick Koly |
| Paul Griffin (Columbia Records) | Andre Chez Lewis |
| Bobby Gregg (Columbia Records) | Jimmy Caltrider |
| Patsy Celtic Band Member | Kyle A. Sanna |
| Patsy Celtic Band Member | Patrick M. Dennis |
| Patsy Celtic Band Member | Nick Baxter |
| Musician Outside Viking #1 | Alan Murray |
| Musician Outside Viking #2 | Mark Gross |
| Musician Outside Viking #3 | Andy Stein |
| Musician Outside Viking #4 | Jean Rohe |
| Texas Prison Working Group #1 | Farley Rene |
| Texas Prison Working Group #2 | Junior Cius |
| Texas Prison Working Group #3 | Travis Patton |
| Texas Prison Working Group #4 | Victor Sho |
| Texas Prison Working Group #5 | Vincent Mp Filliatre |
| Texas Prison Working Group #6 | Amos J. Machanic |
| Man Playing Tambourine | Sunny Jain |
| Vendor Sings Opera | James Archie Worley |
| Paul Stookey (uncredited) | Stephen Carter Carlsen |
| Young Woman in Cocktail Dress (uncredited) | Bridget McGarry |
| Cab Driver (uncredited) | Michael Lepre |
| Folk Festival Stage Manager (uncredited) | Jon Gennari |
