| MOTHERNIGHT | 1996 film in which author Kurt Vonnegut Jr. plays a sad man on the street |
| CIDERHOUSERULES | 1999 film in which author John Irving plays a stationmaster, with "The" |
| GOODSAMARITAN | I go to a sad man in distress? That could be about right |
| WEIRDSCIENCE | 1985 comedy where Robert Downey Jr. plays a bully named Ian (2 wds.) |
| KILGORE | Fictional alter ego of the writer Kurt Vonnegut who appears in the novel God Bless You, Mr Rosewater (7) |
| TROUT | Fictional alter ego of the writer Kurt Vonnegut who appears in the novel God Bless You, Mr Rosewater (5) |
| THEBIRDCAGE | 1996 film in which Robin Williams plays a drag club owner, and a hint to this puzzle's theme |
| JERRYMAGUIRE | 1996 film in which Renee Zellweger plays a single mom who falls for Tom Cruise's title character: 2 wds. |
| EMMA | 1996 film in which Gwyneth Paltrow had her first cinematic leading role |
| VONNEGUT | Author Kurt of the four novels in this puzzle |
| GONZO | Style of reporting in which writers are involved in the events they describe (5) |
| ALEXMILLER | A two-time winner of the Miles Franklin Literary Award, which author released a selection of his notebooks and letters as A Kind of Confession in 2023? (4,6) |
| CHRIS | ___ O'Donnell actor who portrayed Ernest Hemingway in the 1996 film In Love and War |
| OXFORD | City in which author Veronica Stallwood set her series of novels (6) |
| ARKANSAS | Southern U.S. state in which writer John Grisham was born in 1955 (8) |
| BEGGAR | Chocolate-coated Easter item for the man on the street? (6) |
| CATSCRADLE | A 1963 novel by Kurt Vonnegut, Jr |
| THESIRENS | And 16 1959 novel by Kurt Vonnegut, Jr (3,6,2,5) |
| MR | Kurt Vonnegut Jr.'s classic novel God Bless You, ___ Rosewater (2) |
| ROBERTDOWNEY | _ _ Jr. plays Iron Man on the big screen (6,6) |
