Few shows can mix and match genres like Cowboy Bebop. Cowboy Bebop's narrative tone oscillates from funny and laid-back to dark, dramatic, and even scary. All 26 episodes (or "sessions") feature amazing animation and are definitely worth watching with each episode managing to deliver something fresh and unique to the audience.
As a general rule, darker episodes typically advance the story's deeply embedded plot or challenge the characters' to come to terms with their pasts. Lighter episodes tend to be palate cleansers before diving back into more serious themes. This wide tonal variance from session to sessions means Cowboy Bebop has plenty of lighthearted episodes and plenty of darker ones for fans to partake in.
10 Darkest: "Asteroid Blues" Sets A Somber Mood For The Series
Session #1, "Asteroid Blues," establishes how dark Cowboy Bebop can get. The episode opens on a color-sapped, Film Noir-flavored flashback depicting Spike getting ambushed by the Syndicate after his lover Julia stood him up. The rest of the episode doesn't get much lighter. Spike forms a kinship with Katerina, wife of Asimov Solensan, the bounty target he and Jet are hunting. Once Asimov and Katerina are cornered with no escape, Katerina kills her husband and dies shortly after. The episode ends with Jet cooking bell peppers and beef for dinner... except there's no beef.
9 Lightest: "Stray Dog Strut" Is An Episode-Length Chase Sequence
Session #2, "Stray Dog Strut," introduces the first new member of the Bebop crew: Ein, the Data Dog. This episode is much lighter than the series premiere, as the entire episode is basically a comedic chase sequence. Spike and Jet are tracking down Abdul Hakim, a professional pet thief who stole a valuable lab animal known as a Data Dog. Spike stumbles across Hakim by mistake and spends nearly the entire episode chasing him through town. After some misdirection and mistaken identity, Spike and Jet still don't get their bounty, but they do get stuck with Ein.
8 Darkest: "Ballad Of Fallen Angels" Raises The Narrative's Stakes
Session #5, "Ballad Of Fallen Angels," is the first to touch on Spike's past in detail. When his old mentor in the Syndicate, Mao Yenrai, turns up as a bounty mark, Spike realizes it may be time to settle some old scores. What makes this one of the series' darkest episodes is Vicious' entry into the series — Spike's old partner, Mao's murderer, and the closest that Cowboy Bebop has to a main villain.
Vicious and his men capture Faye and hold her captive at a local cathedral to lure Spike out. A duel between the former friends ends with Spike plummeting from the cathedral as his life flashes before his eyes. The dreamy way that Spike falls in slow motion is a memorable scene for fans.
7 Lightest: "Jamming With Edward" Introduces Comic Relief
All of the Bebop crew have their comical moments, but Radical Edward is almost entirely comical moments. Ed debuts in Session #9, "Jamming With Edward," which is also the first time that the Bebop crew visits Earth. The bounty of the episode, a satellite AI which Ed names "Emphu," is the least malicious of the Bebop's quarry. All it does is carve messages into the surface of the Earth, which has already been mostly destroyed by the Astral Gate disaster. In the end, the Bebop crew once again loses their bounty, but they get their fifth and final crewmate.
6 Darkest: "Pierrot Le Fou" Is A Horror Story
Session #20, "Pierrot Le Fou," is the series trying its hand at horror, and it succeeds with terrifying prowess. Spike has a chance encounter with Mad Pierrot, a superpowered serial killer determined to kill the people who created him and anyone who sees him along the way. Spike is completely outmatched by Pierrot and just barely manages to survive their first encounter. Later when Pierrot calls him out to face him at a carnival, Spike comes running despite knowing the danger. Both Spike and Pierrot's gunfight and the flashbacks to Pierrot's creation are bone-chilling.
5 Lightest: "Toys In The Attic" Doesn't Take Itself Seriously
Only a special kind of show can make an Alien homage into one of its silliest episodes. In Session #11, "Toys In The Attic," the Bebop is drifting towards Mars and the crew is enjoying some lazy downtime. Unfortunately, their comfort is short-lived. Soon, a mysterious creature begins attacking and immobilizing the crew one by one, leaving them unconscious and with a toxin coursing through their blood. With Jet and Faye out of commission, Spike launches a one-man mission to destroy the creature. Hilariously, the creature turns out to be a blob monster created by Spike leaving a Ganymede lobster in the fridge for too long.
4 Darkest: "Hard Luck Woman" Is Depressing
Session #24, "Hard Luck Woman" is the penultimate episode of the series. It may not be Cowboy Bebop's darkest session, but it's definitely the saddest. "Hard Luck Woman" focuses mostly on Faye and Ed's mutual desire to reconnect with their pasts. While on Earth, Faye has a chance encounter with an old friend and begins to recover from her amnesia, but she finds her old home in ruins.
Ed, on the other hand, briefly reunites with her father before he runs back off on his own quest to map's Earth asteroid-ridden topography. Taking Faye's advice about finding somewhere to belong, Ed leaves the Bebop crew with Ein to find her own place in the world.
3 Lightest: "Mushroom Samba" Highlights Ed & Ein
In Session #17, the Bebop is out of both rations and fuel. Unsurprisingly, the Bebop crashlands on Jupiter's moon Io, which now resembles a dry, hot, old-fashioned Western town. Ed and Ein head off into town to search for food and eventually bring back some psychedelic mushrooms that cause the others to hallucinate. Spike is trapped on an endless "stairway to heaven," Faye becomes convinced she's underwater and starts swimming, and Jet starts conversing with his Bonsai trees. As the crew deal with the psychedelic effects, Ed & Ein have some misadventures across Io.
2 Darkest: "The Real Folk Blues" Concludes On A Dark Note
Cowboy Bebop ends with Sessions 25 and 26, collectively titled "The Real Folk Blues." As Vicious makes his move to take over the Syndicate, all his old allies are targeted, including Spike and Julia. As Vicious triumphs, the two lovers are reunited, but only briefly. Vicious' men mercilessly shoot down Julia. After one last dinner on the Bebop, Spike flies off, faces down Vicious, and collapses from his wounds with one final word: "Bang." Spike was the only one of the main characters who really came to terms with his past, but in the end, it cost him his life.
1 Lightest: "Cowboy Funk" Feels Like A Parody
Session #22, "Cowboy Funk," is easily the silliest episode in Cowboy Bebop. The episode almost seems like a parody of the anime itself. "Cowboy Funk" focuses on Spike's attempt to capture the "Teddy Bomber," an anarchist bomber who uses bombs hidden in teddy bears to spread chaos. His attempts are undermined by Andy, a bounty hunter who takes the cowboy motif literally. Andy is a parody of the rival trope in shonen anime, and he and Spike are more alike than they think.