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Cameron Diaz’s Biggest Rom-Coms at the Box Office: What the Numbers Show

There’s Something About Mary tops the best-supported romance-centered box-office list for Cameron Diaz, but the evidence does not verify a full top ten.
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There’s Something About Mary leads the romance-centered comedies in Cameron Diaz’s filmography with a reported worldwide gross of $369.9 million. A strict, verified top ten is not supported by the available figures, so this ranking covers the five strongest eligible titles with consistent worldwide totals, then identifies other candidates whose genre or gross is not sufficiently established for a defensible placement.

How this ranking is defined

This list focuses on live-action films in which romance is central, rather than counting every comedy with a romantic subplot. That excludes the Shrek films: their fantasy and family-animation identity makes them a different kind of title, even though they contain romantic elements. It also leaves out ensemble and comedy-drama films when romance is not clearly the main draw.

Grosses below are nominal worldwide figures reported by Box Office Watch’s Cameron Diaz Box Office: Every Movie Ranked, accessed in 2026. They are not adjusted for inflation, and the source does not establish whether its totals include re-releases. These are database figures, not studio financial statements. Because the available evidence does not verify ten qualifying films and totals, presenting ten ranked entries would imply more certainty than the figures support.

The five best-supported romance-centered hits

  1. There’s Something About Mary (1998) — $369.9 million worldwide

    Diaz’s best-supported box-office leader among romance-centered comedies is this story of several men competing for Mary. Box Office Watch reports $369.9 million worldwide. The biographical reference gives a rounded figure of about $369 million, so the film’s position is clear even though sources differ slightly in precision.

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    #1 Best Overall
  2. My Best Friend’s Wedding (1997) — $298.9 million worldwide

    Diaz plays Kimmy in this romantic comedy about a woman confronting her feelings as her close friend prepares to marry. Box Office Watch reports a worldwide gross of $298.9 million.

  3. What Happens in Vegas (2008) — $219.0 million worldwide

    This romantic comedy pairs two strangers who wake up married after a Las Vegas night and then compete over a jackpot. Its reported worldwide gross is $219.0 million.

    Rank #2
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  4. The Holiday (2006) — $205.0 million worldwide

    In this romantic comedy, two women exchange homes and find new relationships. Box Office Watch lists $205.0 million worldwide; a biographical reference describes the result as more than $205 million.

  5. The Other Woman (2014) — $194.3 million worldwide

    This ensemble comedy follows a wife and her husband’s mistresses. It is more romance-adjacent than a straightforward rom-com, so its inclusion depends on how broadly the term is used. Box Office Watch reports $194.3 million worldwide; the film’s reference page reports $196.7 million. The difference is a reminder to treat these totals as source-reported estimates rather than exact, universally agreed figures.

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Why a definitive ten-film ranking is difficult

The available filmography includes other comedies with romantic or relationship storylines, but it does not establish enough genre-specific worldwide totals to fill out ten ranked places responsibly.

  • The Heartbreak Kid is a possible romance-centered candidate, but a worldwide gross was not independently established in the available sources.
  • Sex Tape earned a reported $126.1 million worldwide, but it is an adult comedy about a married couple, not clearly a romance-led film.
  • What to Expect When You’re Expecting earned a reported $88.5 million worldwide, but it is an ensemble comedy with family and relationship storylines.
  • In Her Shoes earned a reported $82.2 million worldwide, but its focus is the relationship between sisters, making it a comedy-drama rather than a straightforward rom-com.
  • The Sweetest Thing is a Diaz-headlined romantic comedy, with a reported $63.1 million worldwide. It is a clear genre fit, but its total falls below the other listed figures.

These figures and genre notes also come from the Box Office Watch filmography; they are context, not a claim that the tracker itself defines which movies count as rom-coms. Counting broader hybrids or family animation would change the scope and potentially the order.

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How to read the grosses

The ranking compares reported worldwide theatrical totals from one tracker, not domestic grosses, ticket sales, profitability, or inflation-adjusted performance. A movie released decades earlier is not being compared on equal purchasing-power terms with a newer one. For some films, reference sources report slightly different totals; using one tracker makes the ordering more consistent, but does not make every figure definitive.

Quick Recap

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