The Guest Director position is held by a different individual each year who is invited by the Telluride Film Festival Directors to join them in the creation of the festival program. The guest director serves as a key collaborator in all of the festival's programming decisions, bringing new ideas and, quite often, overlooked films to Telluride. Below is a list of each guest director followed by the films the director specifically chose to highlight.
| 15th (1988) | Donald Richie | Japan's Cutting Edge | a 2-hour collection of Japanese film dating from 1981 to 1988 | |||
| Remembering Sessue Hayakawa | a two film montage of this film great's first roles in the 1914 film Wrath of the Gods | |||||
| The Dragon Painter | William Worthington | United States | 1919 | |||
| 16th (1989) | John McNaughton | United States | 1986 | |||
| Make Way for Tomorrow | Leo McCarey | 1956 | ||||
| 17th (1990 | Bertrand Tavernier | Justin de Marseille | Maurice Tourneur | France | 1935 | |
| Pursued | Raoul Walsh | United States | 1947 | |||
| 18th (1991) | Laurie Anderson | Danzon | María Novaro | Mexico | 1991 | |
| New Video Art | the first video projection program at the festival which included a series of modern video shorts. | |||||
| 19th (1992) | G. Cabrera Infante | Laughter | Harry d'Abbadie d'Arrast | United States | 1930 | |
| Víctimas del pecado | Emilio Fernández | Mexico | 1951 | |||
| La Virgen de la Caridad | Ramón Peón | Cuba | 1930 | |||
| 20th (1993) | John Boorman | Fear and Desire | Stanley Kubrick | United States | 1953 | |
| Upstage | Monta Bell | 1926 | ||||
| 21st (1994) | John Simon | Il Sorpasso | Dino Risi | Italy | 1962 | |
| One Fine Day | Un certo giorno | Ermanno Olmi | 1969 | |||
| They Shoot Horses, Don't They? | Sydney Pollack | United States | 1969 | |||
| 22nd (1995)[1] | Phillip Lopate | Floating Clouds | Ukigumo | Mikio Naruse | Japan | 1955 |
| The Hard Way | United States | 1943 | ||||
| Welfare | Frederick Wiseman | 1975 | ||||
| 23rd (1996) | B. Ruby Rich | |||||
| 24th (1997) | Peter Von Bagh | |||||
| 25th (1998) | Peter Bogdanovich | |||||
| 26th (1999)[2] | Peter Sellars | Allah Tantou | David Achkar | Guinea, France | 1992 | |
| Dust in the Wind | Hou Hsiao-hsien | Taiwan | 1986 | |||
| 27th (2000)[3] | Edgardo Cozarinsky | |||||
| 28th (2001) | Salman Rushdie | Metropolis | Fritz Lang | Germany | 1927 | |
| Alphaville | Jean-Luc Godard | France | 1965 | |||
| Solaris | Solyaris | Andrei Tarkovsky | Soviet Union | 1972 | ||
| 29th (2002)[4] | Bitter Rice | Riso Amaro | Giuseppe De Santis | Italy | 1949 | |
| Bandits of Orgosolo | Banditi a Orgosolo | Vittorio De Seta | 1961 | |||
| Il Posto | Ermanno Olmi | |||||
| 30th (2003) | They Were Five | La Belle Equipe | France | 1936 | ||
| Un Carnet de Bal | 1937 | |||||
| Panique | 1946 | |||||
| 31st (2004)[5] | Buck Henry | Million Dollar Legs | Edward F. Cline | United States | 1932 | |
| Payday | Don Carpenter | |||||
| Hunger | Sult | Henning Carlsen | Denmark, Norway, Sweden | 1966 | ||
| 32nd (2005) | The Passenger | Professione: reporter | Michelangelo Antonioni | Italy | 1975 | |
| Wanda | Barbara Loden | United States | 1970 | |||
| The Spirit of the Beehive | El espíritu de la colmena | Víctor Erice | Spain | 1973 | ||
| 33rd (2006)[6] | Jean-Pierre Gorin | Maldone | Jean Grémillon | France | 1928 | |
| Stormy Waters | Remorques | 1941 | ||||
| Summer Light | Lumière d'Ètè | 1943 | ||||
| 34th (2007)[7] | Edith Kramer | The Way You Wanted Me | Sellaisena kuin sinä minut halusit | Teuvo Tulio | Finland | 1944 |
| Millions Like Us | Sidney Gilliat and Frank Launder | United Kingdom | 1943 | |||
| Spring Shower (or Marie, a Hungarian Legend) | Tavaszi zápor | Pál Fejös | Hungary | 1932 | ||
| 35th (2008)[8] | Slavoj Zizek | Nightmare Alley | Edmund Golding | United States | 1947 | |
| On Dangerous Ground | Nicholas Ray | 1952 | ||||
| Seconds | John Frankenheimer | 1966 | ||||
| 36th (2009)[9] | Alexander Payne | Day of the Outlaw | Stelios Roccos & James Burroughs | United States | 1959 | |
| The Breaking Point | Michael Curtiz | 1950 | ||||
| Make Way for Tomorrow | Leo McCarey | 1937 | ||||
| 37th (2010)[10] | Michael Ondaatje | The Ascent | Voskhozhdeniye | Larisa Shepitko | Soviet Union | 1977 |
| Confidence | Bizalom | Hungary | 1980 | |||
| Here’s Your Life | Här har du ditt liv | Jan Troell | Sweden | 1966 | ||
| Fat City | John Huston | United States | 1972 | |||
| The Hustler | Robert Rossen | 1961 | ||||
| Mother Dao, the Turtlelike | Moeder Dao, de schildpadgelijkende | Vincent Monnikendam | Netherlands | 1995 | ||
| 38th (2011)[11] | Caetano Veloso | The Apartment | Billy Wilder | United States | 1960 | |
| Aniceto | Leonardo Favio | Argentina | 2008 | |||
| Vivre Sa Vie | Jean-Luc Godard | France | 1962 | |||
| The Grand Maneuver | Les Grandes Manœuvres | René Clair | 1955 | |||
| Black God, White Devil | Deus e o Diabo na Terra do Sol | Glauber Rocha | Brazil | 1964 | ||
| Nordeste: Cordel, Repente E Canção | Tânia Quaresma | 1975 | ||||
| 39th (2012)[12] | Stalker | Andrei Tarkovsky | Soviet Union | 1979 | ||
| Beau Travail | Claire Denis | France | 1999 | |||
| Together | Tillsammans | Lukas Moodysson | Sweden | 2000 | ||
| Lessons of Darkness | Lektionen in Finsternis | Werner Herzog | France, United Kingdom, Germany | 1992 | ||
| The Great Ecstasy of Woodcarver Steiner | Die große Ekstase des Bildschnitzers Steiner | Germany | 1974 | |||
| Baraka | Ron Fricke | United States | 1992 | |||
| Unrelated | Joanna Hogg | United Kingdom | 2007 | |||
| 40th (2013)[13] | Don DeLillo | La Morte Rouge | Victor Erice | Spain | 2006 | |
| The Zapruder Film | United States | 1963 | ||||
| Phillip Lopate | Naked Childhood | L'enfance nue | Maurice Pialat | France | 1968 | |
| Buck Henry | The Terminal Man | Mike Hodges | United States | 1972 | ||
| Michael Ondaatje | Elephant | Alan Clarke | United Kingdom | 1989 | ||
| La Jetée | Chris Marker | France | 1962 | |||
| B. Ruby Rich | One Way or Another | De Cierta Manera | Sara Gómez | Cuba | 1974 | |
| Salman Rushdie | Mahanagar | Satyajit Ray | India | 1963 | ||
| 41st (2014)[14] | Guy Maddin and Kim Morgan | California Split | Robert Altman | United States | 1974 | |
| M | Joseph Losey | 1951 | ||||
| Man's Castle | Frank Borzage | 1933 | ||||
| The Road to Glory | Howard Hawks | 1936 | ||||
| Wicked Woman | Russell Rouse | 1953 | ||||
| Il Grido | Michelangelo Antonioni | Italy | 1957 | |||
| 42nd (2015)[15] | Rachel Kushner | The Mother and the Whore | La maman et la putain | Jean Eustache | France | 1973 |
| My Little Loves | Mes Petites Amoureuses | France | 1974 | |||
| Wake in Fright | Ted Kotcheff | Australia | 1971 | |||
| Cocksucker Blues | Robert Frank | United States | 1979 | |||
| A Day in the Country | Partie de campagne | Jean Renoir | France | 1936 | ||
| Uncle Yanco | Oncle Yanco | Agnès Varda | France | 1967 | ||
| The Mattei Affair | Il Caso Mattei | Francesco Rosi | Italy | 1972 | ||
| 43rd (2016)[16] | Volker Schlöndorff | I Was Nineteen | Ich war neunzehn | Konrad Wolf | East Germany | 1968 |
| It Was in May (or It Was the Month of May) | Byl mesyats may | Marlen Khutsiev | Soviet Union | 1970 | ||
| The Barefoot Contessa | Joseph L. Mankiewicz | United States | 1954 | |||
| Les Enfants terribles | Jean-Pierre Melville | France | 1950 | |||
| The Fire Within | Le Feu follet | Louis Malle | 1963 | |||
| Spies | Spione | Fritz Lang | Germany | 1928 | ||
| 44th (2017)[17] | Joshua Oppenheimer | The Night of the Hunter | Charles Laughton | United States | 1955 | |
| Titicut Follies | Frederick Wiseman | 1967 | ||||
| Hello Cinema | Salaam Cinema | Mohsen Makhmalbaf | Iran | 1995 | ||
| Hotel of the Stars | Jon Bang Carlsen | Denmark | 1981 | |||
| The Umbrellas of Cherbourg | Les Parapluies de Cherbourg | Jacques Demy | France | 1964 | ||
| Even Dwarfs Started Small | Auch Zwerge haben klein angefangen | Werner Herzog | West Germany | 1970 | ||
| 45th (2018)[18] | Jonathan Lethem | Angel | Ernst Lubitsch | United States | 1937 | |
| Bigger Than Life | Nicholas Ray | 1956 | ||||
| Never Cry Wolf | Carroll Ballard | 1983 | ||||
| The Tarnished Angels | Douglas Sirk | 1957 | ||||
| To Be or Not to Be | Ernst Lubitsch | 1942 | ||||
| The White Meadows | Keshtzarhaye sepid | Mohammad Rasoulof | Iran | 2009 | ||
| 46th (2019)[19] | Pico Iyer | Late Autumn | Akibiyori | Yasujirō Ozu | Japan | 1960 |
| When a Woman Ascends the Stairs | Onna ga kaidan o agaru toki | Mikio Naruse | ||||
| The Makioka Sisters | Sasame-yuki | Kon Ichikawa | 1983 | |||
| Mr. and Mrs. Iyer | Aparna Sen | India | 2002 | |||
| Under the Sun | V luchakh solnca | Vitaly Mansky | Czech Republic, Russia, Germany, Latvia, North Korea | 2015 | ||
| 47th (2020) | The 47th Telluride Film Festival did not occur in 2020 due the COVID-19 pandemic. | |||||
| 48th (2021)[20] | Barry Jenkins | West Indies: The Fugitive Slaves of Liberty | West Indies ou les Nègres marrons de la liberté | Med Hondo | France, Mauritania, Algeria | 1979 |
| Chocolat | Claire Denis | France | 1988 | |||
| Looking for Langston | Isaac Julien | United Kingdom | 1989 | |||
| Garden | Adi Barash | Israel | 2003 | |||
| Russian Ark | Russkij kovcheg | Alexander Sokurov | Russia | |||
| Kahlil Joseph: Selected Works | Kahlil Joseph | United States | - | |||
| 49th (2022)[21] | Kantemir Balagov and Kira Kovalenko | L'Atalante | Jean Vigo | France | 1934 | |
| Elegy of a Voyage | Elegiya dorogi | Aleksandr Sokurov | France, Russia, Netherlands | 2001 | ||
| Getting to Know the Big, Wide, World | Poznavaya belyy svet | Kira Muratova | Soviet Union | 1978 | ||
| Oasis | 오아시스 | Lee Chang-dong | South Korea | 2002 | ||
| Where Is the Friend's House? | Khane-ye dust kojast | Abbas Kiarostami | Iran | 1987 | ||
| The Wonders | Le meraviglie | Alice Rohrwacher | Italy, Switzerland, Germany | 2014 | ||
| 50th (2023)[22] | Steve McQueen | Zero for Conduct | Zéro de Conduite | Jean Vigo | France | 1933 |
| Mira Nair | The Music Room | Jalsaghar | Satyajit Ray | India | 1958 | |
| Alfonso Cuarón | Jonah Who Will Be 25 on the Year 2000 | Jonas qui aura 25 ans en l'an 2000 | Alain Tanner | France-Switzerland | 1976 | |
| Rachel Kushner | Juvenile Court | Frederick Wiseman | United States | 1973 | ||
| Ethan Hawke | All That Jazz | Bob Fosse | United States | 1979 | ||
| Adam Curtis | The Long Good Friday | John Mackenzie | United Kingdom | 1980 | ||