Tommy Caldwell

Caldwell and fellow climbers Beth Rodden, John Dickey and Jason 'Singer' Smith were held hostage for six days by rebels in Kyrgyzstan in August 2000. Caldwell pushed a lone captor, Ravshan Sharipov, off a cliff, and subsequently escaped to government soldiers. They later learned that Sharipov survived the fall. A book about their ordeal, Over the Edge: The True Story of Four American Climbers' Kidnap and Escape in the Mountains of Central Asia was written by Greg Child. A follow-up article, "Back from the Edge", was published in Outside magazine the following year. Caldwell gave a filmed lecture "How Becoming a Hostage and Losing a Finger Made Him a Better Climber".

Caldwell accidentally sawed off much of his left index finger with a table saw in 2001. Doctors were able to reattach the severed portion, but Caldwell decided he didn’t want the useless finger, which doctors said he would never be able to use to climb with again, and the damaged part of the finger was later permanently removed.

Caldwell and Beth Rodden married in 2003, and subsequently divorced in 2010. In 2010 he met photographer Rebecca Pietsch. They married in 2012. The couple have a son, Fitz, and a daughter, Ingrid Wilde, and live in Estes Park, Colorado .

In May 2004, he completed the first free ascent (FFA) of Dihedral Wall. In 2005, he and Beth Rodden—swapping leads—made the third and fourth free ascents of The Nose. Two days later, on October 16, Caldwell free-climbed The Nose in less than 12 hours. A few days later, Caldwell climbed The Nose in 11 hours, descended the East Ledges, and then climbed Freerider, topping out 12 hours later – the first ascent of two El Capitan free climbs in 24 hours. On El Capitan, Caldwell has also free-climbed: Lurking Fear, Muir Wall, West Buttress, Salathé, Zodiac, Magic Mushroom, The Dawn Wall, and New Dawn.

Caldwell was one of the climbers featured in the 2009 film Progression. The film discussed his quest to climb the Dawn Wall, and it was after seeing the film that Jorgeson contacted Caldwell to join him in the effort.

In January 2015, Caldwell and Kevin Jorgeson completed the first free climb of the Dawn Wall of El Capitan in Yosemite National Park, after six years of planning and preparation. Their 19-day ascent of the Dawn Wall was considered by some as the hardest successful rock climb in history. The following year Czech climber Adam Ondra free climbed the Dawn Wall in 8 days. Ondra praised Caldwell and Jorgeson saying, "Tommy and Kevin put so much effort into the climb and faced so many question marks and logistical problems that I cannot really compare my effort to theirs. I had it prepared, had all the knowledge. I knew it was possible".

The Dawn Wall, a documentary following Caldwell and Jorgeson on their free climb of the Dawn Wall, was released on September 19, 2018. The documentary was directed by Josh Lowell and Peter Mortimer.

Caldwell appeared in the documentary Free Solo, released on September 28, 2018, about Alex Honnold's free solo ascent up El Capitan in Yosemite National Park. In the documentary, Caldwell is seen working with Honnold to prepare for the climb, and is interviewed about Honnold and rock climbing.