Top 10 Guest Stars of 'Two and a Half Men': Charlie Sheen and Ashton Kutcher Era

A Look Back at Some of the Most Memorable Cameos

10. Carol Kane

Carol Kane, known for her roles in films like "The Princess Bride" and "Portnoy's Complaint," appeared in the sixth season episode "Thank God for Scoliosis." She played Shelly, Melissa's aging hippie mother, who was described as "not completely right in the head" due to her heavy marijuana use.

The actress's performance was praised for its quirkiness and comedic timing.

9. Emily Rose

Emily Rose, who starred in the horror film "The Ring," guest-starred in the same episode as Kane. She played a waitress who catches the attention of both Charlie and Jake.

Rose's character provided a brief but memorable love interest for both brothers.

8. Conan O'Brien

Late-night talk show host Conan O'Brien made a cameo appearance in the seventh season episode "Mmm, Fish. Yum." He played a therapist who counsels Charlie after he is arrested for drunk driving.

O'Brien's self-deprecating humor and witty banter made his appearance a standout.

7. Jon Lovitz

Comedian Jon Lovitz appeared in multiple episodes throughout the series. He played Herb Melnick, Alan's uptight and neurotic neighbor.

Lovitz's character brought a touch of absurdity to the show, often getting into bizarre and awkward situations.

6. Martin Sheen

Charlie Sheen's real-life father, Martin Sheen, appeared in the eighth season episode "Chocolate Diddlers or My Puppy's Dead." He played Charlie's father, who visits for Thanksgiving and stirs up trouble.

The episode showcased the comedic chemistry between father and son, with Martin Sheen holding his own against his son's outrageous antics.

5. Jenny McCarthy

Model and television personality Jenny McCarthy appeared in the ninth season episode "The Squat and the Hover." She played a massage therapist who gives Charlie a happy ending.

McCarthy's appearance was controversial at the time, with some viewers criticizing the show for promoting prostitution. However, she brought her signature blend of sex appeal and humor to the role.

4. Miley Cyrus

Before she became a global superstar, Miley Cyrus appeared in the tenth season episode "Hookers, Hookers, Hookers." She played Missi, a teenage runaway who stays with Walden and Alan.

Cyrus's performance was praised for its maturity and depth, showcasing her talent beyond singing.

3. Ashton Kutcher

After Charlie Sheen's departure from the show, Ashton Kutcher was brought in to replace him. Kutcher played Walden Schmidt, a wealthy internet billionaire who moves into Charlie's house.

Kutcher's addition to the cast brought a new dynamic to the show, and his chemistry with Jon Cryer and Angus T. Jones was undeniable.

2. Courtney Thorne-Smith

Courtney Thorne-Smith appeared in the final two seasons of the show as Lyndsey McElroy, Walden's love interest and eventual wife.

Thorne-Smith's character was a strong and independent woman who brought a new level of maturity to the show.

1. Josh Groban

Singer-songwriter Josh Groban appeared in the series finale, "Of Course He's Dead." He played himself, serenading Walden and Lyndsey at their wedding.

Groban's performance provided a fitting and emotional end to the long-running sitcom.