Celebrity Breakups of '09

She's been dating her "Ghost Whisperer" co-star Jamie Kennedy for the majority of 2009, but at the beginning of the year, Jennifer Love Hewitt was still attached to her former fiance, Ross McCall. The couple called off their engagement on January 5.

Brit comedian Russell Brand has been keeping Katy Perry warm since September, but the "I Kissed a Girl" singer's former flame -- Gym Class Hereos frontman Travis McCoy -- had that honor until the twosome dissolved a few months into '09.

Following her dramatic split with Hugh Hefner, Holly Madison hooked up with Vegas illusionist Criss Angel, but she disappeared from his arm in February of this year.

Rihanna and Chris Brown's split was undoubtedly one of 2009's biggest breakups. And, while many people assume the couple ended things in February following their horrific domestic violence dispute, we tend to believe that Rihanna didn't cut him off completely until months later.
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With 12 years separating them, we weren't that surprised when "Heroes" hotties Hayden Panettiere and Milo Ventimiglia ended their on-again/off-again relationship in February.

John Mayer broke unlucky-in-love Jennifer Aniston's heart for the last time in March, three weeks after the power couple lit up the red carpet at the 81st Academy Awards. Which A-lister will John devastate next? Stay tuned.
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After three years of separation and enough stress to last a lifetime, Robyn Gibson filed for divorce from hubby Mel in April. Six months later, his latest gal pal, Russian musician Oksana Grigorieva, gave birth to his eighth child, a daughter named Lucia.

On the June 22 episode of "Jon and Kate Plus 8," it was announced that Jon and Kate Gosselin were separating and that a divorce was in the works. Six months later on December 18, the paperwork was completed, and the troubled reality stars were no longer legally bound to one another.

We'll never quite understand why Miley Cyrus dumped her sexy underwear model beau Justin Gaston back in June after nine months of dating, but apparently the teen queen has moved on with ease. It's been reported that she and her "Last Song" co-star Liam Hemsworth are now an undercover item.

Dallas Cowboys quarterback Tony Romo dumped Jessica Simpson on July 9 -- the night before her 29th birthday -- after dating her for nearly 20 months. What a sweet guy!

On July 21, Kelis gave birth to her and Nas' first son, Knight, two months after she filed for divorce from the rapper. On July 23, a New York City judge ordered Nas to pay $55,000 per month in child and spousal support.

Sean and Robin Wright Penn's relationship has been a roller coaster ride for the past few years, but on August 12 the gorgeous and talented mother of three filed for divorce, declaring that she has no plans to reconcile with her Oscar-winning ex.

Three and a half years after tying the knot in a private ceremony in Montecito, California, Avril Lavigne said see ya later boi to her sk8er boi/hubby Deryck Whibley and filed divorce papers on October 9.

A few short weeks ago, news broke that Jake Gyllenhaal and Reese Witherspoon amicably parted ways after three years as Hollywood's cutest couple. Rumor has it that Reese wasn't ready to commit, but we'll probably never know the real reason why they ended things. Any ideas?