April 20, 1999 - In a New York City deli, a woman is enjoying a slice of cheesecake with her family when she notices something vaguely familiar about the young man dining alone in the next booth. The young man returns her gaze with icy blue eyes and a clear, unspoken message, "Don't you dare tell your teenage daughter that it's me, Leonardo DiCaprio.”

Poor Leo. How could he have known at the time that the teenage girl he snubbed in that deli (on her 18th birthday, no less!) would one day become a supremely influential entertainment writer for Film.com? He never could have guessed that nine years into the future, on the eve of the release of his spy thriller Body of Lies, she'd be tasked with rating the best and worst films of his career.

Just how much of an impression had this incident made on her? Would she use this opportunity for revenge, or would she swallow her pride and just pick out his top and bottom five films like she was supposed to? Read on to find out.

Top Five

1. The Departed
Out of Leo's three collaborations with Martin Scorsese, there's no question this is the one that had audiences spending the most time on the edge of their seats. This crime drama was so intense, it made a scene between only a paranoid Leo and a ringing cell phone one of the most terrifying cinematic moments in recent memory.

2. Catch Me if You Can
Proving he could be much more charming on screen than he was in that deli, Leo perfectly embodied the role of Frank Abagnale Jr., a true-life con artist who became the youngest person ever on the FBI's most wanted list. Leo's nuanced performance made it easy for audiences to relate to Tom Hanks's cranky FBI agent character, who developed an odd sort of affection for Frank even as he devoted his life to putting an end to his highly creative crimes.

3. Gangs of New York
Daniel Day-Lewis is one of those pesky actors who only shows up every couple of years to spoil Oscar races and get critics salivating. But Leo held his own against Day Lewis's Bill the Butcher in this epic about early New York.

4. William Shakespeare's Romeo and Juliet
Director Baz Luhrmann went to stylistic extremes to prove he could make Shakespeare relevant to modern audiences. But Leo's performance as Romeo was so heartfelt, the teenage girls in the audience didn't need any other help interpreting the Bard's ancient dialogue.

5. Titanic
It's kind of tough for me to put Titanic on this list. Leo and his co-star Kate Winslet have both topped their performances in this epic many times over since it became the highest-grossing film of all time in 1997. But somehow, I suspect people will still be reciting "You jump, I jump" and "I’ll never let go" for much longer than they'll remember any lines from any of the other movies on this list.

Bottom Five

5. The Aviator
Just as it was hard to put Titanic in Leo's top five, it's hard to put The Aviator in the bottom five. There are some great things about The Aviator, and most of them involve Leo's performance (as well as any scene involving Cate Blanchett as Katharine Hepburn). But Howard Hughes lived such a (sorry, there's no choice but to make the pun here) huge life, even focusing on his early years left too much room for the script to wander.

4. The Man in the Iron Mask
Anything he did after Titanic was going to feel like a letdown. But it's still inexcusable that Leo failed to connect with audiences in this film, considering he was playing two roles, and therefore had two chances.

3. The Beach
Leo was finally able to kill his image as a teen idol in this strange island saga. Unfortunately, he was also able to temporarily kill his image as an actor who makes good movies.

2. The 11th Hour
When he chose to produce and narrate this environmentally conscious documentary, he managed to do the impossible. He failed to match the charisma of Al Gore.

1. Don's Plum
I'm actually taking a guess here that this is Leo's all-time worst movie. Guessing is all I can do because I haven't seen the film, as it was never legally released in the United States. Leo and his longtime BFF Tobey Maguire successfully sued to have this low-budget indie blocked from distribution, claiming they only participated in it as a favor to a film student friend who told them it would never be released. If Leo and Tobey were willing to mar their public images by suing a struggling filmmaker friend to keep people from seeing this movie, it must have been really bad.

Feel free to agree, disagree, or share your own heartbreaking stories about being snubbed by celebrities in the comments section below.

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