1. The Break-Up
#1,237 most popular movie yesterdayThe Break-Up stars Jennifer Aniston and Vince Vaughn in a comedy about a couple who, well, breaks up but continues to live together. Forwarded as a romantic comedy, it presents a relatable tale of love and its complications, much like the awkward situations and entanglements in My Boss's Daughter.
6 movies like The Break-Up...2. The Hot Chick
#1,482 most popular movie yesterdayThe Hot Chick shares the goofy, over-the-top humor that defines My Boss's Daughter. A body-swap comedy featuring Rob Schneider and Rachel McAdams, it's a laugh-out-loud story that explores identity and empathy in a hilariously unconventional way.
8 movies like The Hot Chick...3. She's Out of My League
#2,201 most popular movie yesterdayFor those who enjoy the underdog protagonist of My Boss's Daughter, She's Out of My League offers a similar vibe. The movie follows an average Joe who meets the perfect woman, whom he believes is out of his league, and it’s his journey of navigating this mismatched romance.
7 movies like She's Out of My League...4. Fool's Gold
#3,271 most popular movie yesterdayFool's Gold, starring Matthew McConaughey and Kate Hudson, is a treasure-hunt adventure that has the same comedic tone as My Boss's Daughter. This romantic comedy is packed with action, providing a lively viewing experience for those who fancy a mix of genres.
6 movies like Fool's Gold...5. Just Married
#3,888 most popular movie yesterdayJust Married, starring Ashton Kutcher and Brittany Murphy, is a wild rom-com that fans of My Boss's Daughter will appreciate for its mix of slapstick humor and heartwarming romance. The movie tells the story of a young couple dealing with the mishaps of their disastrous honeymoon, which puts their marriage to the test.
8 movies like Just Married...6. Employee of the Month
#4,334 most popular movie yesterdayA workplace comedy like My Boss's Daughter, Employee of the Month features Jessica Simpson and Dane Cook in a story about competitors turned lovers. Audiences who enjoy lighthearted tales of workplace shenanigans will find this to be an amusing escape.
7 movies like Employee of the Month...7. Guess Who
#4,646 most popular movie yesterdayGuess Who, featuring Ashton Kutcher yet again, puts a comedic twist on meeting the parents. Like My Boss's Daughter, it is filled with awkward situations and cultural clashes that make for a humorous narrative when a boyfriend meets his girlfriend’s family for the first time.
8 movies like Guess Who...8. Blind Date
#5,071 most popular movie yesterdayBlind Date involves the classic setup of a date gone wrong, which is the central theme of My Boss's Daughter when a man watches over his crush’s pet. This film presents Bruce Willis and Kim Basinger in an equally chaotic romantic escapade filled with unpredictability and wit.
8 movies like Blind Date...
My Boss's Daughter
Similar Shows & Recommendations

Movies like My Boss's Daughter (2003)
If you're looking for some great movies that are a lot like My Boss's Daughter, here is our list of similar films: