Alyssa Milano began her acting career at the age of 11 by appearing in the coming-of-age feature film, Old Enough, in 1984. Since then, the former child star has had an up and down career in film and television, including her long-running stint as Samantha Micelli on the popular '80s sitcom Who's The Boss? and a spate of not-so-well-received films released in the 1990s.
By the end of the decade, Milano rebounded with her witchy role as Phoebe Halliwell in Charmed, which she played for eight years and 178 episodes. Including her many made-for-TV movie appearances and TV guest spots, Alyssa Milano's big and small screen career continues to thrive in 2021 and beyond.
10 Fear (1996) 6.2
One of the few well-received films Milano starred in during the 1990s included Fear, the creepy stalker-thriller starring Mark Wahlberg and Reese Witherspoon. The former plays David, a seemingly perfect suitor for Nicole (Witherspoon), who becomes violently obsessed with becoming her boyfriend.
Milano plays Nicole's close friend, Margo, who is physically abused by David at a high-school party. As David's possessive nature escalates, his actions turn lethal, forcing Nicole's parents to get involved when he invades their house with his gang.
9 The Blue Hour (2007) 6.4
The Blue Hour is a lesser-known drama that interweaves the lives of several multi-ethnic characters on the fringes of Los Angeles. Milano leads the way as Allegra, a woman who lives with her husband, an Armenian camera repairman, on the East Bank of the Los Angeles River.
The other three main characters include a Mexican graffiti artist, a Black blues musician, and an English retiree, all of whom struggle to stay afloat in an unforgiving city. The Blue Hour marks the first film Milano made after her eight-year run on Charmed.
8 Old Enough (1984) 6.4
Milano's first feature film credit belongs to Old Enough, a coming-of-age movie in which she plays a neighborhood kid named Diane. The central drama concerns the adolescent friendship among two young girls from different sides of the socioeconomic divide.
Karen (Rainbow Harvest) is a street-smart 11-year-old girl from an abusive, poverty-stricken family who meets Lonnie (Sarah Boyd), a girl from an affluent part of New York. In spending the summer together, the two learn about each other's unique views, customs, lifestyle choices, and family backgrounds.
7 Where The Day Takes You (1992) 6.6
Milano plays a hard-luck prostitute named Kimmy in the star-studded Where the Day Takes You, a neo-noir thriller about a group of wayward runaways surviving the streets of Los Angeles any way they can. The group follows King (Dermot Mulroney), a streetwise criminal who introduces the others to a life of drugs, prostitution, violent crime, and the like.
Will Smith makes his big-screen debut in the film, which also features Sean Astin, Ricky Lake, David Arquette, Kyle MacLachlan, Balthazar Getty, Christian Slater, and Lara Flynn Boyle.
6 Commando (1985) 6.7
According to IMDb, Milano's best movie is the 1985 Arnold Schawarzenegger action film Commando. The plot revolves around the kidnapping of young Jenny Matrix (Milano) and the dogged, deadly revenge campaign her father John Matrix exacts to get her back safely.
To find his daughter, Matrix teams with innocent bystander Cindy (Rae Dawn Chong) to waylay several heavily-armed soldiers en route to a fortified mansion headed by Bennett (Vernon Wells), an evil villain with his own vengeful agenda.
5 Insatiable (2018 - 2019) 6.5
Milano's most recent recurring TV character is Coralee Armstrong in the Netflix original series, Insatiable. The dark satirical comedy takes aim at the culture of beauty pageants as seen through the eyes of bullied teenager Patty Bladell (Debby Ryan).
When Patty spends a summer losing weight with plans to avenge her bullies, washed-up lawyer and beauty pageant zealot Bob Armstrong (Dallas Roberts) takes the girl under his wing and attempts to turn her into a winning contestant. Milano stars as Bob's wife, with whom Patty constantly butts heads.
4 Wet Hot American Summer: 10 Years Later (2017) 6.9
To qualify for the best TV shows of her career, Milano has to appear in at least five episodes. As such, her five-episode stint as Renata Delvecchio in Wet Hot American Summer: 10 Years Later ranks among her top 5, according to IMDb. The show is a sequel to the 2001 film Wet Hot American Summer and a prequel to the 2015 spinoff series Wet Hot American Summer: First Day of Camp, and both go on to explain some of the storylines and strange plot points of the movie.
Renata serves as the temporary nanny for Ben (Adam Scott) and McKinley's (Michael Ian Black) newborn daughter Ashley in the miniseries, often giving the couple false compliments over their parenting skills.
3 Mistresses (2013 - 2016) 7.1
ABC's Mistresses is a swanky soap opera mystery adapted from the British series of the same name. Milano headlines as Savi Davis, one of four self-empowered best friends who do everything possible to keep their steamy extramarital affairs a secret.
Savi is a successful lawyer no longer happy with her husband Harry (Brett Tucker) and their inability to have children. As Savi expands her sexual horizons, her unpredictable half-sister, Josslyn (Jes Macallan), adds more drama to her life. Milano appeared in exactly half of the episodes (26/52) before leaving the series in 2014.
2 Charmed (1998 - 2006) 7.1
Other than Samantha Micelli, Phoebe Halliwell is the longest-running character Milano has played during her television career. Along with her witchy sisters, Piper (Hollie Marie Combs), Prue (Shannen Doherty), and Paige (Rose McGowan), the Charmed Ones use their inherent powers to defeat evil forces.
Phoebe obtains the power of premonition, allowing her to witness the future and the past. Along with expert martial art skills, she later develops powers of levitation and empathy to help her fight alongside her sisters.
1 My Name Is Earl (2005 - 2009) 7.7
Milano played Billie Cunningham in 10 episodes of My Name is Earl, a former criminal who, at one point, marries the titular star (Jason Lee). However, after the lottery-winning antihero neglects his new bride, Billie steals his list of dream purchases and runs off to the Camendites.
When Earl realizes his mistake and chases Billie to the village, she refuses his expression of love and sends him packing with a goodbye kiss, his list, and an extra $72,000. My Name is Earl won five Primetime Emmys during its four seasons on the air.
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June 19, 2021 at 12:00AM
