His win wasn’t exactly a surprise: McConaughey, 44, who lost an extreme amount of weight to play AIDS patient Ron Woodruff in the film, has been unstoppable this award season. He picked up Best Actor trophies everywhere from the Golden Globes to the SAG Awards to the Independent Spirit Awards. He immediately became a Twitter sensation after the Globes, starting with the “alright, alright, alright” line and making everyone excited for a McConaughey sweep of awards.
Who would have thought? Over the course of two decades, McConaughey went from starring in stoner flicks to becoming a rom-com king to HBO show star to Academy Award winner. Here’s a look back at some of his most iconic career moments leading up to his first-time Oscar win:
1993: Appears as Wooderson in Richard Linklater’s now-classic “Dazed and Confused”
2001: Stars as Generic Rom-Com Hero in “The Wedding Planner” opposite Jennifer Lopez
2003: Further cements Rom-Com King status in “How to Lose a Guy in 10 Days” with Kate Hudson, though his character in this one is a bit more complex
2012: Takes everyone by surprise with a dynamic performance as a stripper in “Magic Mike” — even gets Oscar buzz, though that doesn’t pan out.
2014: Gets raves in HBO drama “True Detective” for his philosophical cop alongside Woody Harrelson
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