The cast of the TV series Angel, a spinoff of Buffy the Vampire Slayer.
Warner Bros.

Though crossing over intermittently. the show follows Angel (David Boreanaz), fellow Sunnydale transplants Cordelia Chase (Charisma Carpenter) and Wesley Wyndham-Pryce (Alexis Denisof), and a growing cast of new characters fight monsters, solve mysteries, and avert the occasional apocalypse.

Like Buffy before it, Angel had a knack for reinvention, and it evolved from a monster-of-the-week procedural to a grim serialized family drama to a workplace dramedy throughout its five seasons. It may not have the same legendary reputation, but Angel could be as thrilling, heartbreaking, or hilarious as Buffy, and these 10 episodes stand out among the very best the Whedonverse has to offer.

10. A Hole in the World (season 5, episode 15)

Wesley Wyndham-Pryce holds the dying Fred Burkle in "A Hole in the World"
20th Television

It may be shocking to some readers to see A Hole in the World listed so far down our list, but in truth, we almost didn’t include it at all. This episode, in which adorable science whiz Winnifred Burkle (Amy Acker) dies a slow, horrible death that gives birth to new character Illyria (also Acker), is one of the cruelest hours in the history of television, an example of writer-director Joss Whedon flaunting his power over the audience for his own jollies.

Whedon absolutely loves to “kick the puppy,” to pull the rug out from under his characters the moment they find any sort of peace or happiness, and much like Tara’s murder in season 6 of Buffy, Fred’s agonizing demise only one episode after finally getting together with Wesley feels like the show’s creator pointing and laughing at us for daring to experience hope or joy.

A Hole in the World is also undeniably great. Its opening act has the levity and jocularity of your typical monster-of-the-week episode, lulling the audience into a false sense of security. Once the stakes are set, the team’s determination becomes a loving tribute to Fred and her impact on their lives. (Wesley shooting a Wolfram & Hart staffer in the shin for flippantly interrupting his research is a great bit.) But as hope erodes, A Hole in the World becomes a showcase for Acker and Denisof as actors. Fred’s deterioration is heartbreaking to watch, not only because of Acker’s tearful performance, but because of how Denisof plays against it. Wesley wants to put on a brave face for Fred, but as the clock runs out, you can see it’s absolutely killing him to watch her suffer. We are observing the death of a beautiful future, in real time. 

9. Orpheus (season 4, episode 18)

Willow Rosenberg regards a floating red orb in the Angel episode "Orpheus"
20th Television

It’s hard to deny that Angel’s fourth season is an uneven mess, particularly since Carpenter went public with her allegations of abusive behavior by Whedon regarding her pregnancy. It’s hard not to read Cordelia’s possession by the goddess Jasmine, which turns her into the season’s primary antagonist, as a petty retaliation for the impact her family leave would have on the show. Still, the story arc in which Angel’s demonic persona Angelus breaks loose and wreaks havoc is a series highlight, even if it’s nested in the middle of a lot of weirdness. We could have picked any chapter in this six-part story for our list, but we’ll go with the grand finale, Orpheus, in which the desperate Angel Investigations team recruits the only other person who’s ever restored Angel’s soul — Sunnydale’s own Willow Rosenberg (Allyson Hannigan).

Of course, Orpheus has more going for it than an exciting guest star, or even two exciting guest stars, as vampire slayer Faith (Eliza Dushku) is also in the mix for this storyline. The episode’s A-plot sees Angelus and Faith in a shared magical hallucination that has them revisit some of the darkest moments in Angel’s past, when he was wandering America with a soul, but without purpose. This century-spanning retrospective ends with a one-time-only metaphysical matchup between Angel and Angelus, as they throw down for dominance over their body and their future. It’s Angelus’ last appearance on the show (except in flashback), making it the climax of an internal battle that had been raging since we first met him on Buffy.

8. Conviction (season 5, episode 1)

Charles Gunn stands in a courtroom wearing a slick suit in the Angel episode "Conviction"
20th Television

Season 5 of Angel is essentially a whole new show that mashes its established action/adventure format with the bones of a legal drama and, to an extent, a workplace comedy. Team Angel’s mission to “help the helpless” is put on hold as it takes the reins of the proudly evil law firm Wolfram & Hart and tries, against all odds, to use its resources for good. Conviction puts Angel’s old mission and his new job at cross purposes in a big way, when one of the firm’s nastiest clients threatens to release a deadly virus if he’s found guilty in court. The story sees each member of the team working the problem from their own angle, efficiently reestablishing each of their roles in the show’s new status quo, as well as the internal forces they’ll have to contend with in order to change the workplace culture at Wolfram & Hart. For example, where it was once customary to, say, massacre a classroom full of children in order to contain a threat, this is frowned upon by the new management. 

Perhaps the episode’s coolest twist — cooler even than the addition of Spike (James Marsters) to the cast — is the radical change in the role of Charles Gunn (J. August Richards) on the show. Once the team’s “muscle” and Everyman, Gunn accepts an offer from Wolfram & Hart to have their entire law library downloaded into his head, making him the superintelligent leader of their legal department. It’s great to see Gunn working in a whole new lane, but just as interesting to see the ways in which his new skills haven’t changed him. He is, essentially, the same guy with a new confidence, which becomes tragic when that confidence slips away later in the season. 

7. Five By Five/Sanctuary (season 1, episodes 18 & 19)

Buffy Summers stands in Angel Investigations in the episode "Sanctuary"
20th Television

Buffy Summers (Sarah Michelle Gellar) makes only two appearances on Angel, and most fans might prefer to see the romantic tragedy I Will Remember You make our top 10. But for our money, we find Buffy’s final visit to Los Angeles, in which she and Angel are at odds over the fate of murderous rogue vampire slayer Faith, to be far more interesting. Faith comes to LA after waking from a coma and hijacking Buffy’s body in a recent Buffy the Vampire Slayer episode, and accepts a contract from Wolfram & Hart to assassinate Angel.

Before long, however, it becomes clear that Faith is trying to throw herself into being “evil” because she believes she deserves to die. After torturing Wesley, her former watcher, Faith goads Angel into a fight and, essentially, attempts “suicide by cop.” Angel, who recognizes Faith’s remorse and helplessness from his own life, instead offers her shelter and mentorship. This presents a problem when Buffy shows up in town to apprehend her, and Angel won’t allow it.

Faith is an excellent foil for Angel, an opportunity for him to help someone fight similar (if not literal) demons to his own. Faith would reappear on Angel a few more times, and always seemed more at home here than on Buffy. But more than that, Sanctuary is essentially the final nail in the coffin for Buffy and Angel’s romance, as they’re forced to acknowledge that they’ve begun to build separate, incompatible lives. When he was a supporting character on her show, Angel’s life could revolve around Buffy. Now, as the leading man, he has his own goals, his own crew, and there’s simply no room for either of them to play second fiddle for the other. It makes for terrific drama, as well as a good explanation for why neither of them appears on the other’s series for a while.

Also, Buffy and Faith fight a helicopter. That alone is enough to secure this episode a place on this list.

6. Spin the Bottle (season 4, episode 6)

Nestled into the incredibly grim darkness of season 4 is this comedic episode from Joss Whedon in which a spell gone wrong reverts the memories of each member of Team Angel to the age of 17. It’s an opportunity to gauge just how much these characters have grown since we first met them, and to get a peek into the early lives of the ones we haven’t known very long. Cordelia is once again the self-centered brat we first met on Buffy, a far cry from the compassionate, functional adult she’s become since acquiring her visions. Wesley is even more buffoonish and useless than when he first arrived in Sunnydale, the total opposite of his present, brooding avenger persona. Gunn arguably gets the least interesting change, merely becoming more defensive and suspicious, but it’s fun to see Fred as a stoner and a conspiracy freak, and Angel — or should we say Liam — as a man out of time who mistakes automobiles for screaming metal demons.

Sure, Whedon himself had already pulled a similar gimmick in the Buffy episode Tabula Rasa, wiping the Scooby Gang’s memories and letting the cast play different versions of their characters, but Spin the Bottle adds an extra dash of nostalgia for longtime fans. According to this episode’s DVD commentary, the entire story was reverse-engineered from the desire to let Denisof play the comically useless version of Wesley again, which got so many laughs on set that it actually prolonged the shooting schedule. The cast is clearly having a ball with this one, and in a year that’s mostly bummers and head-scratchers, Spin the Bottle provides some welcome comic relief. 

5. Life of the Party (season 5, episode 5)

Lorne looks into the camera in the Angel episode "Life of the Party."
20th Television

Season 5 has a handful of comedic episodes (with Smile Time being an obvious pick), but none of them are as consistently funny as Life of the Party, written by The Tick creator Ben Edlund. In this episode, Lorne (Andy Hallett) goes overboard in planning Wolfram & Hart’s Halloween bash, which ends up having a death toll. Lorne is the member of Team Angel who was the most natural fit at W&H as the head of the entertainment division. He’s a schmoozer, a people-pleaser, and a demon who does his best to reserve judgment on the people with whom he works.

So, when Angel’s do-gooder reputation jeopardizes the firm’s biggest public event of the year, Lorne implores him to extend an olive branch to some of LA’s evil elite. Meanwhile, Lorne’s workload has gotten so untenable that he’s resorted to having his sleep removed, which has some unexpected side effects. Hilarity ensues.

Life of the Party makes terrific use of the entire ensemble, as Lorne’s new ability to write fortunes rather than read them puts the rest of Team Angel into compromising situations that have them playing against type. Wesley and Fred get stupid drunk, Angel and Eve (Sarah Thompson) resolve their sexual tension on the office floor, Gunn keeps peeing everywhere, and Lorne’s subconscious frustrations have manifested physically into a big, murdering muscleman. What’s not to like? Even more than the gimmicky Smile Time and its Muppet mayhem, Life of the Party is the quintessential “workplace comedy” episode of Angel, and we wish the series had run long enough to produce a lot more of them. 

4. Waiting in the Wings (season 3, episode 13)

Summer Glau as the prima ballerina in the Angel episode "Waiting in the Wings"
20th Television

Compared to concurrent shows Buffy and Firefly, Whedon has relatively few writing or directing credits on Angel. Before taking over as showrunner in season 5, only a handful of episodes received his personal stamp, and even these tended to be less experimental or groundbreaking than the Buffy episodes that bore his name. Waiting in the Wings, however, is Whedon through and through, a format-breaking hour in which the gang from Angel Investigations gets dolled up for a night at the ballet.

There, sparks fly between the team’s various will they or won’t they couples as they are swept up in both the stirring emotion of classical dance and, of course, a magical mystery. As it happens, this ballet company has been unstuck in time, and its prima ballerina (Summer Glau) is forced to repeat her performance forever for the pleasure of a creepy warlock (Mark Harelik). Angel and Cordelia may become trapped, too, if they can’t find a way to break the spell.

Waiting in the Wings is a ‘shipper’s dream, with the spell forcing would-be lovers Angel and Cordelia to reenact a torrid affair from a century ago, and the formal occasion and deadly stakes finally inspiring Fred and Gunn to act on their feelings for each other, much to the dismay of the lovesick Wesley. It’s also a dreamy, methodically shot episode, as one might expect from Whedon, who aspired toward a filmic atmosphere for many of his episodes. In place of the usual soundtrack, the episode is scored almost completely by Adolphe Adam’s ballet Giselle. Just as the trip to the theater is a special occasion for the characters, Waiting in the Wings feels like a momentous, classy affair for the audience as well.

3. Are You Now or Have You Ever Been (season 2, episode 2)

Angel in the 1950s with his hair slicked back in the episode "Are You Now Or Have Your Ever Been"
20th Television

From the early days of Buffy, audiences have been acquainted with the terrible guilt that Angel bears for the atrocities committed by his soulless demon self, Angelus, in the 18th and 19th centuries. However, until his spinoff, precious little was known about Angel’s life between the restoration of his soul in 1898 and his getting his act together to help the Slayer in 1996. In Are You Now or Have You Ever Been, Angel becomes fixated on a deserted, supposedly haunted hotel, the Hyperion, and asks Cordelia and Wesley to investigate it.

Angel leaves them in the dark as to the source of his curiosity, but the audience is treated to a series of flashbacks to the mid-1950s, during which Angel was a resident at the Hyperion. A total recluse, Angel tries to avoid entanglements with the other residents, but when trouble arrives at his doorstep, he’s forced to choose between maintaining his anonymity and correcting an injustice. Set against the backdrop of the Red Scare and the McCarthy hearings, Are You Now… is a portrait of both humanity and Angel at their worst.

In addition to being a solid hour of standalone period drama, Are You Now… depicts Angel in a new light, both in the flashbacks and in the present day. In the ’50s, he’s ensouled but embittered, a man worn down by witnessing centuries of conflict motivated by petty bigotry. In the present day, we see Angel facing his guilt over a shameful incident in his life for which he cannot blame the demon inside of him. His failure at the Hyperion was a human one, driven by the same fear and selfishness seen in the worst of humanity. It’s also a sin for which he may still be able to make meaningful restitution.

2. Sleep Tight/Forgiving (season 3, episodes 16 & 17)

Wesley Wyndham-Pryce looking weary in the Angel episode "Sleep Tight"
20th Television

When Wesley Wyndham-Pryce is introduced during the third season of Buffy, he is essentially the show’s C-3PO, a prissy and uptight buffoon whose role is primarily to make his fellow watcher Giles look cool and rugged by comparison. After three years of growth on Angel, Wesley is barely recognizable — he’s a ruggedly handsome warrior and tactician with sad eyes and a wounded heart. Like everyone else at Angel Investigations, Wesley has been through hells both figurative and literal, but his defining moment comes when a prophecy leads him to believe that Angel, his friend and ally, is destined to devour his own newborn son, Connor.

In Sleep Tight, after desperately searching for any way to discredit the prophecy, and also witnessing Angel’s recent uncharacteristically violent behavior, Wesley makes the fateful decision to kidnap Connor and skip town — only to have his throat slit by Justine (Laurel Holloman), who delivers the infant to Angel’s sworn enemy, Holtz (Keith Szarabajka). The episode ends with a devastating cliffhanger, as Angel discovers Wesley’s betrayal and Wesley bleeds out on his front lawn, with no help in sight.

The tragedy only deepens in the next episode, Forgiving, as Angel and company learn just how thoroughly they’ve been played by the alliance of Holtz, Lilah (Stephanie Romanov), and the time-traveling demon Sahjahn (Jack Conley). By the end of the second hour, Holtz has absconded with baby Connor into an inaccessible hell dimension, with no hope of rescue. Even Sleep Tight’s ending pales in comparison to the devastating final scene of Forgiving, in which Angel visits the ailing Wesley in the hospital and tries to smother him to death with a pillow.

This is the dramatic peak of the series, the point at which the conflict between the protagonists feels most irreconcilable. It speaks to the strength of the plotting and characterization of Angel that these two heroes could both break our hearts so thoroughly, and yet still elicit sympathy. They’ve both done something terrible, and yet it’s hard to say that either of them is wrong. It’s a perfect portrait of the complexity and moral ambiguity that Angel was created to explore, painted in a dozen shades of gray.

1. Not Fade Away (season 5, episode 22)

Four people stand in the rain in Angel.
Warner Bros.

While it’s unfortunate that Angel was cut short after five seasons, it’s hard to imagine a better finale for the series than Not Fade Away. From the beginning, Angel has been fighting an uphill battle against the entrenched evils of the world, represented by the interdimensional law firm Wolfram & Hart. Though he’s been able to carve out a few victories and even gain control over W&H’s Los Angeles branch, it’s become clear that he will never be able to permanently defeat the gods and monsters that rule over the Earth. At best, he can give them a bloody nose, and perhaps some good can be done while the beasts recover.

In Not Fade Away, Angel and his allies decide to take the only shot they’ve got and embark on a suicide mission to wipe out the Circle of the Black Thorn, a cabal of demons that carries out evil’s will on Earth. They succeed in settling all family business, assassinating the Black Thorn’s entire leadership, but as expected, Wolfram & Hart’s otherworldly “senior partners” bring the hammer down hard. The series ends with Angel, Spike, Gunn, and Illyria squaring off against a literal army of demons, giants, and a fire-breathing dragon. With no hope of victory, our heroes ready their weapons and charge into battle, and the screen cuts to black.

‘Angel’ Series Finale 15th Anniversary: David Boreanaz Reveals How That Final Fight Played Out

Ignore the comics continuation — this is the end of the story, and that’s good. Angel is not, and never has been, a tale of good triumphing over evil. It’s been about good struggling against evil, whatever the cost. Throughout the series, Angel practically never gets a clean win over the forces of darkness. Every victory is short-lived and comes at a terrible cost, but he keeps fighting. Angel’s final act is this same idea on a grander scale. It’s the biggest win Angel’s crew can possibly manage, it will have a limited impact, it will cost them everything, and they’re going to do it anyway, because that’s what makes them champions.

There is, and cannot be, a finish line, which is why Angel signs away the Shanshu Prophecy before the final battle. Even if he stopped the apocalypse mentioned in the ancient scroll and received his humanity as a reward, there would just be another apocalypse to fight afterwards, as there have been several before. The fight is only over when they’re dead, and since we don’t actually witness Angel and company’s demise, we are left to imagine that it goes on forever.

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