Matt Damon as Odysseus in a screenshot from the trailer of the 2026 Nolan film – if my recollection of the film serves correctly, this is from his scene with Circe (fair use)
(9) CIRCEAD
Yes, okay, Circe only appears in one book of the Odyssey – Book 10 – and doesn’t even have that book to herself with Odysseus, albeit her scenes within that book are among the most iconic in the Odyssey, but her liaison with him has been the source of enduring fascination and influence ever since. Artists, poets, and writers have added to that liaison, most notably through adding her son with Odysseus, Telegonus.
Even in the Odyssey itself, her role extends beyond her book as she gives him critical guidance to find his way to the underworld in the following book.
Also, since he was with her for one year of the ten years of the Odyssey, it seems only apt that she have one entry out of ten in my Top 10 Odysseys.
Calypso as depicted by Charlize Theron in a screenshot from the trailer for the 2026 Nolan film (fair use)
(10) CALYPSONY
And yes – it might be pushing it to give Calypso her own odyssey within the Odyssey. Like Circe, she has her own book within the Odyssey – Book 5 – although she is also mentioned in two other books, Books 1 and 7.
However, since Odysseus spends the large majority of the ten years of the Odyssey – indeed, 70% of them or seven of the ten years – with Calypso on her island, I feel she’s only due her place here. In a very real sense, in duration and in significance, most of the Odyssey is Calypso’s odyssey.
Also, she poses perhaps the most substantial temptation to Odyssey not to return home, over and above being the longest obstacle to his homecoming in duration of years – and that is her promise of immortality. For the narrative and thematic significance of that alone, she deserves her own odyssey within the Odyssey.