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Dempsey was nominated for Best Performance by an Actor in a Television Series–Drama at the 2006 Golden Globes for the role. It's financially rewarding but there comes a point where how much is enough, really?

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His first major television role was a three-episode stint as Will Truman's closeted sportscaster boyfriend on Will & Grace.

He went on to play the role of Aaron Brooks on Once & Again.

This was followed by the teen comedy Can't Buy Me Love in 1987 with actress Amanda Peterson and Some Girls with Jennifer Connelly in 1988.

In 1989, Dempsey had the lead role in the films Loverboy with actress Kirstie Alley and Happy Together with actress Helen Slater.

He was successful in landing a lead role in Sweet Home Alabama (2002), a surprise box office hit.

He has since starred in other films, including Enchanted (2007), Made of Honor (2008), Valentine's Day (2010), Flypaper (2011), Freedom Writers (2007), Transformers: Dark of the Moon (2011), and Bridget Jones's Baby (2016).

Before landing the role, Dempsey auditioned for the role of Dr. He also appeared in two episodes of the later Grey's spinoff Private Practice, playing the same character of Dr. The relationship his character had with Meredith Grey (Ellen Pompeo) on screen has received a lot of praise and positive reactions - portraying a love story far more realistic than the usual "happy ever after" the chemistry between the two made this love story the center one of the series.

In January 2014, he signed a two-year contract to remain on Grey's Anatomy, then in its tenth season, that would ensure his participation for potential 11th and 12th seasons.

He also voiced the character Kenai in Brother Bear sequel Brother Bear 2, replacing Joaquin Phoenix.

Dempsey's most recent roles include the 2008 film Made of Honor as Tom, and the 2010 romantic comedy Valentine's Day; the latter film follows five interconnecting stories about Los Angelinos anticipating (or in some cases dreading) the holiday of love.

He has been the face of L'Oreal and Versace and was featured in ads for Serengeti sunglasses.

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