Alyssa Milano stands as one of the hottest evolutions of an actress ever. She started off playing Sam, the tomboy daughter on the ABC sitcom Who’s The Boss? She got good lines but as the show went on, Milano grew up into a truly beautiful young woman who ended the show in college and showing off a lot more. After a few lean years, Milano took a major step in changing her image. In 1994, she starred in the direct-to-video thriller Embrace of the Vampire which involved her stripping down to show off a very hot body. She followed it with Poison Ivy 2, again showing her body off and proved ready for adulthood.
This all led to Milano’s more famous role of Phoebe Halliwell on Charmed. One of three sisters who discover they’re from a long line of witches, Phoebe had the power to see the future. From the start, the show pushed a great chemistry with her, Holly Marie Combs (Piper) and Shannen Doherty (Prue) with each lady showing off a very hot side. The show had a great eight-year run with Milano becoming a co-producer and maintaining Phoebe’s great drive. That included a long romance with demon Cole (Julian McMahon) that ended badly and yet also some very sexy scenes. There have been plenty of great moments of Phoebe along the show’s run with Milano showing off her body a bit but also fun humor and even some dramatic chops. Here are 15 of the most memorable moments of Milano on Charmed and how she was clearly everyone’s favorite Charmed One.
15. First Time Out
The first time Phoebe used her powers has to rank among the most memorable. Like many pilots, “Something Wicca This Way Comes” has some rough stuff as the series was a long way from finding its feet. It starts out with Phoebe having spent years away from her sisters traveling and only coming back after their grandma dies. They’re distant before reading the Book of Shadows which unlocks their powers as the Charmed Ones. Phoebe is hit first as she’s biking when she gets a vision of a pair of roller-bladers being run down by a car. Seeing them coming, she wipes her bike out in front of them, taking a trip to the hospital to save her first innocents.
The pilot shows how Phoebe is the most gung-ho about being witches, encouraging Prue to learn her powers and then aiding Piper in stopping a warlock who’s been killing witches to steal their powers. It ends with them joining together in their first vanquishing and realizing it’s their destiny to be together. Milano had the role well in hand from the start and showing her nice style which would make Phoebe a key reason to watch the show.
14. Kiddie Behavior
Milano was fantastic with the special effects stuff as well as the drama of the role of Phoebe. But she managed to make episodes fun even when she was playing much younger than her sexy age. In “Once Upon a Time,” Phoebe and Prue have to save a fairy but because they’re adults, they can’t see her. The fairy tries to solve that by spraying them with dust to make them “innocent” again. This has the side effect of making the girls think they’re about six years old again. This leads to a hysterical scene of them acting up at P3 with bad singing and giggling and Piper forced to treat them like kids until the dust wears off.
A few years later, in “Cheaper by the Coven,” the spirit of the girls’ grandmother, Grams, comes by to help out with baby Wyatt. Worried about the bickering of the sisters, Grams tries to use a spell to stop it but it backfires and turns the girls into bickering teenagers. Phoebe is great as a wicked brat, accepting an award at a ceremony in a way that makes folks think she’s drunk and then fighting Piper’s teasing on her boss/boyfriend. It takes Grams, their dad and the spirit of their mother to break the spell but both episodes show how Milano makes even being a kid look funny.
13. Meeting Cole
Cole Turner was introduced in the season three premiere, “The Honeymoon Is Over” and one look was enough to make Phoebe smitten. A suave and debonair man, Cole seemed the latest in the long line of would-be suitors unaware of the girls’ nature. During a fight in the middle of a trial, Piper uses her powers to freeze everyone in the courtroom except witches and demons. The sisters fight the demons in human form outside…at which point, Cole suddenly starts moving among the frozen crowd. He then uses powers to fry a demon before returning to make himself appear human once more. Cole had been born to a human father and demon mother and long hated for his “half-breed” nature. Over a century and a half years old, he saw seducing Phoebe as the best way to get at the Sisters.
Soon, Cole and Phoebe were a couple with some very steamy hookups and the chemistry between them fantastic. To keep his cover, Cole helped the sisters out before they finally figured out what he really was. This led to Phoebe getting Cole to a cemetery, ready to use a potion to destroy him. Cole told her he could have killed her a dozen times…but he couldn’t because he was in love with her. It was the beginning of a very complex romance that seemed to go well but ended in a lot of heartache.
12. Burned Alive
It was rare for Charmed to tackle pure drama but “Morality Bites” sure had that in spades. It opens with Phoebe convincing the girls to use their powers to teach a lesson to a troublesome neighbor. Phoebe is then hit with a premonition of herself burned at the stake. Casting a spell to figure this out, the girls find themselves whisked into a future where magic is not only publicly known but witches are hunted down. Piper and Leo have a daughter but are divorced. Prue owns her own business but has turned into the very sort of arrogant millionaire she hates. And Phoebe is in jail facing execution for using her powers to kill a man. At first, she doesn’t believe it but future Leo reveals that the guy had killed a good friend of Phoebe’s and she did it for revenge.
Piper and Prue are worried to realize their future selves had indulged in magic for their own gain. Leo says Phoebe has to die for the greater good but her sisters are ready to break her out. However, Phoebe tells them that Leo was right; she crossed the line and has to pay or other witches will suffer in a hunt. Realizing she means it, the sisters hug her and then watch as Phoebe is set on fire. They’re whisked back to the present where they stop themselves from punishing that neighbor…who would have been the guy leading the anti-witch crusade in the future. It was a key episode as the sisters realize the consequences of magic and Phoebe seeing her dark side on display.
11. Mummy Dancer
This was a rather shameless way to show off Milano’s body but she sure did great with it. In “Y Tu Mummy Tambien,” the sisters have to deal with Jeric, an ancient Egyptian demon who’s trying to find a new body for the spirit of his beloved. He kidnaps Phoebe and does the possession on her. This leads to Milano providing one of her hottest moments of the series by donning an Egyptian harem outfit for a belly dance. It’s a very sexy shot and Milano clearly knows the attention is on her with her smooth moves. It’s interrupted by Cole who wants Phoebe for himself and strikes a bargain with Jeric to get him a new body in the form of Paige. The sisters are able to undo the process with Phoebe reacting badly to the nutty outfit she’s in. It’s among the many times Phoebe got stuck in some sort of very wild outfit but it also ranks among the best to show how Milano could cast a very sexy spell in the part.
10. Starting The Cliché
A running gag through the early years of the show was Phoebe complaining about the classic clichés of witches as hags who rode broomsticks. In “All Halliwell’s Eve,” the sisters host a Halloween party and Phoebe decides to don a “protest costume” of Elvira, Mistress of the Dark. It’s a hot look for her, a tight black outfit and bustier and dark wig and she pulls it off nicely. Of course, it can’t be a normal Halloween as the girls suddenly find themselves yanked through time to 1670 Virginia. A coven of witches need their help to save them from hunters but the time trip has shaken up the girls’ powers. They do end up helping the witches out and in a hilarious bit, Phoebe realized that the entire broomstick thing was begun by her using one to escape being hanged. In either the Elvira outfit or 17th century clothing, Milano shines and it’s a fun look at the history the sisters have and playing with witchy tropes.
9. Pregnant And Possessed
Phoebe would probably never claim to be mother material. However, she didn’t have much of a choice when, after seemingly vanquishing Cole in season four, she discovered she was carrying his child. She did her best to handle it but worried about the child inheriting his dad’s demonic powers. In “Womb Raider,” Phoebe starts to be affected deeply by the kid such as electrocuting a doctor during a sonogram. There’s also her snapping to belt Paige across the face and then meekly say “the baby made me do it.” Milano does a funny job handling the whole thing.
However, it gets more dramatic when Phoebe is kidnapped by the demonic Seer and taken away. It turns out that the Seer was the one who arranged this pregnancy and the “baby” is really just the power of the evil Source. The Seer absorbs it only to be overwhelmed by the power, allowing the sister to defeat her. While happy in some ways, Phoebe clearly does regret not being able to have a child of her own and hoping for another shot down the road. It was a good episode that gave Milano comedy but also showed her heart too.
8. Under The Sea
As the fifth season of the show began, Phoebe had gotten a job as an advice columnist and moving on with her life. However, she’s thrown when Cole pops up alive and well to cause some trouble and Phoebe wanting to get rid of him. She’s met up by Mylie (future Emmy-winner Jaime Pressley), who wants love advice. When a car splashes them, Mylie’s legs turn into a tail as she’s a mermaid. She’s trying to find her true love and the sisters help (needed as Mylie’s emotions are causing storms across the city). In the middle of it all, Phoebe is turned into a mermaid herself and naturally, the sight of Milano in the getup is amazing. The clam shell top looks great as does the tail, her long hair lush and a bright smile on her face. She actually decides to stay in the ocean first to be away from Cole but eventually realizes she belongs on land. It’s one of the best of Phoebe’s many sexy transformations and a look only Milano could pull off.
7. Evil Queen
The Cole/Phoebe relationship reached its zenith in season four as they were married. However, Cole soon began falling back into darkness to become the Source, basically the leader of all evil forces. At first worried, Phoebe soon joined with him, thinking their love could overcome his darkness. Discovering she was pregnant with Cole’s child just increased that so Phoebe was willing to turn on her sisters. This led to her joining Cole as the “Queen” of the Underworld, clad in some very nice black outfits and doing her best to show a dark attitude. It didn’t work as Phoebe just couldn’t go through with destroying Piper, Prue, and Cole ended up sacrificing himself to save her and free her from this dark connection.
Another take on Phoebe as the evil Queen came in the 100th episode as Cole, desperate to have Phoebe back, manipulates time so they stayed married and evil. Again, Milano got to show off nicely in some very hot dark outfits. However, Cole finds her with another demon as he realizes that in any timeline, he and Phoebe would have broken up. He’s killed to set the timeline right and off the show as Phoebe got to show a lot more of her dark side off.
6. Hear No Evil
Quite often, Charmed was at its best balancing the action and drama with pure comedy as the actresses excelled at it. A great case is “Sense and Sense Ability.” A witch goes after the sisters by causing a monkey to strike each one for the classic “see no evil/hear no evil/speak no evil” monkey statues. Paige loses her voice, Piper her sight and Phoebe her hearing. This leads to a great comedy bit of the trio trying to communicate as Piper stumbles around, Paige tries charades and Phoebe is yelling at the top of her lungs. It’s a funny sequence as they try to figure out what to do when they can’t even communicate right. A highlight is when Paige writes down “KILL MONKEY” on a notepad and Phoebe tells Piper “Paige is advocating violence against the monkey.” They manage to get on the same page in order to finally subdue the witch yet the episode shows the great comic timing Milano had to match her great looks for Phoebe.
5. Being Paige
When Rose McGowan joined the show in season 4, the series played with the sisters trying to handle a new dynamic. Paige was shown a little jealous at how Phoebe seemed to have it all together and learning to fight demons and wishes she could be like her while mixing a spell. It literally blows up in her face and causes the two to switch bodies. Milano does a brilliant job aping McGowan’s mannerisms and speech patterns with “Phoebe” suddenly a little nervous and unsure of herself. This leads to some interactions with Cole, who’s baffled at first but realizes what’s going on when he tries to kiss “Phoebe.” It also has an interesting touch as each sister uses the switch to get Piper to share her real feelings about Paige part of the family. There’s fun stuff like Paige checking her new body out and sucking on a lollipop and the switch ends up helping the girls defeat a demon. This was a great sequence to show how Milano could be fun even when not playing herself.
4. Blushing Bride
For the first three seasons of the show, Phoebe had a lot of bad romances. This included short-lived guys who she had to cut off due to her wiccan responsibilities and more than once, found herself falling for a demon. That changed in season four when she met Cole and despite his evil side, he was soon drawn to her and wanting to be good to be with her. It culminated with their wedding and Phoebe in a glorious bridal gown. Sadly, Cole manipulated the wedding in a scheme to seize dark power and make Phoebe think he was still the good guy. Starting a marriage on such a bad note was one of many reasons it just didn’t work out.
3. 50s Gal
A great comedy episode for Phoebe, “Lost and Bound” was mostly focused on the sisters trying to keep safe a 10-year-old whose fire powers made him a target of his demon parents. A big turn was Cole proposing to Phoebe and she accepted. This was just after Phoebe talked of her love for the old TV show Bewitched. Soon after, Phoebe starts to act like a typical 1950s housewife, all docile and lecturing people on manners. She also starts flashing black and white which gets everyone confused. This leads to a funny scene where Cole finds her in the bath and tells her she has to step up and take more command of things. Phoebe rises up, covered only in bubbles just as Paige enters and covers her eyes from “full frontal Phoebe.” It turns out the ring was cursed to infect Phoebe with thoughts of what kind of wife she thought Cole would want. She dumps it to get back to normal but it shows even as a lady from a supposedly straight-laced time, Milano could be very hot.
2. Genie Phoebe
Phoebe was always a good-hearted soul and her big issue was often in trusting people who turned out to be not so nice. Such a case is in “I Dream of Phoebe” as she and Chris (Piper and Leo’s son from the future) find a lamp containing a genie named Jinny who begs for help from a demon. Phoebe decides to immediately wish for Jinny to be free only to get sucked into the lamp. It turns out that Jinny is really a demon herself and the lamp always needs a genie. This means Phoebe, now in a blue harem outfit and blonde hair (she openly complains “why do I always get stuck with the blonde wig?!”)
This plays into the storyline as Chris needs Piper and Leo to get together so he can be born. He thus wishes for them to “sleep together” only the wish backfires to put them in a coma. Eventually, they’re able to get Jinny back into the lamp to free Phoebe from this but the sight of Milano as a genie was one of her sexiest looks on the show.
1. Double The Phoebe, Double The Fun
Alyssa Milano had a great time here playing against herself in the episode “The Importance of Being Phoebe.” Increasingly losing it, Cole ends up at a strip club where demons are the entertainment. One dancer, Kaia, pushes him down, then proceeds to shape-shift into Phoebe to give him a lap dance. Hit by inspiration, Cole decides to use her as part of a plot to tear the sisters apart and take over the Manor. Naturally, Phoebe is appalled when Kaia shows up as her and a fun bit of Kaia using it to figure out how to sound like Phoebe. So you have Milano playing a performance of her own performance as Kaia sells the sisters on being under Cole’s power so they strip “Phoebe” of her powers and doing a good job mimicking the normal Phoebe’s appearance and mannerisms. Naturally, it’s all set right in the end but still showcases how Milano could have some fun with the part playing both Phoebe and a take on herself nicely.