
The wonderful friendship of Adam Sandler and Drew Barrymore: “I love this man so much and have always believed in him”
Whether watching Happy Gilmore or Punch Drunk Love, the work of Adam Sandler remains a constant source of light and intrigue, with the actor forging a career from light-hearted comedies in the 1990s before making a brave pivot into dramatic acting, with an achingly vulnerable performance in Paul Thomas Anderson’s modern love story.
However, while the actor has found a new fan base through his work with the Safdie brothers, his audience was widened after starring in a number of romantic comedies alongside Drew Barrymore and Jennifer Aniston, becoming long-time collaborators with both women. This has led to films such as 50 First Dates and The Wedding Singer, with Sandler and Barrymore’s electric chemistry defining them as one of the ultimate on-screen romantic couples, with both actors working together multiple times since their first film together in 1998.
However, their convincing nature as a movie couple has led to many speculations about their relationship in real life, with some fans speculating that there might be more to their connection than just professionalism. However, they have maintained that their relationship is strictly business despite years of swoon-worthy romantic performances.
In the years passing, both have expressed nothing but love and admiration for each other and have maintained a close friendship over the years. When introducing Sandler at an awards ceremony, Barrymore said, “I love this man so much and have always believed in him. I know everyone supports you because you have earned everyone’s respect. You deserve the best, you give your best, and you are the best. I love you dearly.”
Sandler also reflected on their friendship over the years, saying, “Growing up with her is going to be a good time. She has a great spirit, and I love her.”

How many movies has Adam Sandler made with Drew Barrymore?
Over the years, both actors have starred in three films together, with the pair meeting in 1998 for the Frank Coraci film The Wedding Singer, which follows a local wedding singer who forms a relationship with waitress Julia while trying to organise her wedding. The pair subsequently worked together in 2004 for 50 First Dates, directed by Peter Segal, in which Barrymore plays a woman called Lucy with no short-term memory who is seduced by a man called Henry, realising that they can fall in love repeatedly as she won’t remember their dates.
And finally, both actors starred in Blended, also directed by Frank Coraci in 2014, about two lovelorn people who are encouraged to date by their friends, which goes horribly wrong, leading to disastrous consequences when the pair find themselves on the same holiday with their children.
…but which Adam Sandler movie made the most money?
While 50 First Dates grossed over $280million at the box office when it was released on Valentine’s Day in 2004, it was nowhere near the most financially successful of Sandler’s films, with his work on the Hotel Transylvania films topping his personal charts, with the third film making $528.5m at the global box office.
However, the 2010 film Grown Ups was also very commercially successful, with the comedy earning $272m at the global box office.