| MALKOVICH | Being John ___: 1999 film in which the titular actor appears as a version of himself (9) |
| BOWL | University Challenge began as a version of US quiz show College ___. (4) |
| SIDNEY | Oprah-produced documentary about the titular actor-activist |
| EALES | John ___, 1999 Rugby World Cup-winning captain (5) |
| SONATA | Not as a version for piano, perhaps |
| VENUSBERG | Setting of Richard Wagner's 1845 opera Tannhauser, in which the titular character meets the Roman goddess of love (9) |
| ORSONBEAN | Dr. Lester portrayer in "Being John Malkovich" |
| BREAKSOUT | Escapes, appears as a rash on body? (6,3) |
| CIDERHOUSERULES | 1999 film in which author John Irving plays a stationmaster, with "The" |
| KUMAILNANJIANI | Silicon Valley actor who starred as a semifictional version of himself in 2017's The Big Sick: 2 wds. |
| SMITH | Will _, actor who played a fictionalised version of himself in The Fresh Prince Of Bel-Air (5) |
| AMERICAN | 1999 film in which Stifler's mom pours a glass of scotch and remarks, "Aged eighteen years...just th |
| SCREEN | ___ time, the amount of a film in which an actor appears (6) |
| METEOR | Which small fragment of matter from outer space appears as a streak of light as it burns up in the atmosphere (6) |
| EPISODES | TV sitcom in which U.S. actor Matt LeBlanc played a fictional version of himself (8) |
| GALAXYQUEST | 1999 film in which Sigourney Weaver plays an actress who plays an officer on a spaceship: 2 wds. |
| GODOT | Waiting for ___: 1953 play by Samuel Beckett in which the titular character never appears (5) |
| DOCTORFAUSTUS | Christopher Marlowe play in which the titular character gives his soul to the devil (6,7) |
| MAGNOLIA | 1999 film in which Miriam Margolyes and Ricky Jay were among the ensemble cast (8) |
| FIGHTCLUB | What not to talk about, per a 1999 film (In this answer, note the first 2 Letters + the last letter) |
