Editing River Phoenix (section)

===1986–1993: Breakthrough and final projects===
[[File:River Phoenix and Martha Plimpton.jpg|thumb|left|Phoenix and [[Martha Plimpton]] on the red carpet at the [[61st Academy Awards]] in 1989|upright=1]]

Phoenix had a significant role in [[Rob Reiner]]'s popular coming-of-age film ''[[Stand by Me (film)|Stand by Me]]'' (1986), which made him a household name at 16. Filming started on June 17, 1985, and ended in late August 1985, making Phoenix 14 for most (if not all) of the movie. ''[[The Washington Post]]'' opined that Phoenix gave the film its "centre of gravity".<ref name="The Independent"/> Phoenix commented: "The truth is, I identified so much with the role of Chris Chambers that if I hadn't had my family to go back to after the shoot, I'd have probably had to see a psychiatrist."<ref name=Tribune/> Later that year, Phoenix completed [[Peter Weir]]'s ''[[The Mosquito Coast (film)|The Mosquito Coast]]'' (1986), playing the son of [[Harrison Ford]] and [[Helen Mirren]]'s characters. "He was obviously going to be a movie star," observed Weir. "It's something apart from acting ability. [[Laurence Olivier]] never had what River had."<ref name="The Independent"/> During the five-month shoot in [[Belize]], Phoenix began a romance with co-star [[Martha Plimpton]], a relationship which continued in some form for many years.<ref name="The Independent"/> Phoenix was surprised by the poor reception for the film, feeling more secure about his work in it than he had in ''Stand by Me''.<ref name=Tribune/>

Phoenix was next cast as the lead in the teen comedy-drama ''[[A Night in the Life of Jimmy Reardon]]'' (1988), but was disappointed with his performance: "It didn't turn out the way I thought it would, and I put the blame on myself. I wanted to do a comedy, and it was definitely a stretch, but I'm not sure I was even the right person for the role."<ref name=Tribune>{{Cite web|url=https://www.chicagotribune.com/news/ct-xpm-1988-03-27-8803040033-story.html|title=The Rise of River Phoenix|first=Iain|last=Blair|website=Chicago Tribune |date=March 27, 1988 |access-date=July 22, 2013}}</ref> Also in 1988, Phoenix starred in ''[[Little Nikita]]'' alongside [[Sidney Poitier]]. During this time, the Phoenix family continued to move on a regular basis, relocating over forty times by the time Phoenix was 18. Phoenix purchased his family a ranch in [[Micanopy, Florida]], near [[Gainesville, Florida|Gainesville]], in 1987, in addition to a spread in Costa Rica.<ref name=Esquire/>

[[File:River Phoenix.jpg|thumb|150px|Phoenix at the [[61st Academy Awards]]' Governor's Ball, March 1989]]

His sixth feature film was [[Sidney Lumet]]'s ''[[Running on Empty (1988 film)|Running on Empty]]'' (1988), for which the 18-year-old Phoenix received [[National Board of Review Award for Best Supporting Actor]] and nominations for a [[Golden Globe Award for Best Supporting Actor – Motion Picture|Golden Globe Award]] and an [[Academy Award for Best Supporting Actor|Academy Award]], becoming the [[List of oldest and youngest Academy Award winners and nominees#Youngest nominees 4|sixth-youngest]] Academy Award nominee in the category.<ref>{{Cite web|last=Renfro|first=Kim|title=The 31 youngest Oscar nominees of all time|url=https://www.insider.com/youngest-oscar-nominees-2018-2|access-date=April 17, 2021|website=Insider}}</ref><ref>{{Cite web|last=Evry|first=Max|title=The 25 Youngest Oscar Nominees of All Time|url=https://www.mtv.com/news/2802405/youngest-oscar-nominees-winners-of-all-time/|archive-url=https://web.archive.org/web/20170301024436/http://www.mtv.com/news/2802405/youngest-oscar-nominees-winners-of-all-time/|url-status=dead|archive-date=March 1, 2017|access-date=April 17, 2021|website=MTV News}}</ref> Phoenix jumped to his feet during the ceremony when [[Kevin Kline]] beat him to the Oscar. "I had to stop River from running to hug Kevin," recalled his mother Arlyn. "It never crossed his mind that he hadn't won".<ref name=Esquire/> In 1989, he portrayed a young [[Indiana Jones (character)|Indiana Jones]] in the prologue of the box-office hit ''[[Indiana Jones and the Last Crusade]]'', the third installment of the ''[[Indiana Jones]]'' franchise, directed by [[Steven Spielberg]] and starring Harrison Ford.

Phoenix was photographed by [[Bruce Weber (photographer)|Bruce Weber]] for ''[[Vogue (magazine)|Vogue]]'' and was spokesperson for a campaign for [[Gap Inc.|Gap]] in 1990. He starred with Kevin Kline, [[Tracey Ullman]], [[Joan Plowright]] and [[Keanu Reeves]] in the 1990 comedy film ''[[I Love You to Death]]''. Phoenix had met Reeves while Reeves was filming the 1989 film ''[[Parenthood (film)|Parenthood]]'' with Phoenix's brother, [[Joaquin Phoenix|Joaquin]], and girlfriend, [[Martha Plimpton]]; however, Phoenix had reportedly auditioned for Bill in Reeves' then-current film ''[[Bill & Ted's Excellent Adventure]]'' before the role was taken by [[Alex Winter]].<ref>{{cite news|url=http://www.pajiba.com/seriously_random_lists/bill-teds-excellent-adventure-movie-facts.php |title='Bill & Ted's Excellent Adventure' Movie Facts |newspaper=Pajiba |date=May 8, 2018 |access-date=March 13, 2019 |last1=Smith |first1=Jodi }}</ref><ref>{{cite web |last=Hughes |first=Kat |date=March 4, 2019 |title=Ten Things You Never Knew About 'Bill And Ted's Excellent Adventure' |url=http://www.thehollywoodnews.com/2019/03/04/ten-things-you-never-knew-about-bill-and-teds-excellent-adventure/ |access-date=March 13, 2019 |publisher=The Hollywood News}}</ref>

He co-starred with [[Lili Taylor]] in the acclaimed independent picture ''[[Dogfight (film)|Dogfight]]'' (1991), directed by [[Nancy Savoca]]. In the romantic coming-of-age drama set in San Francisco, Phoenix portrayed a young U.S. Marine on the night before he is shipped off to Vietnam in November 1963. Taylor remarked that Phoenix suffered because he could not distance himself from his character: "He also hadn't gotten into any [drugs]—he was just drinking then, too. It was different... That was actually a hard part for him, because it was so radically different from who he was. He was such a hippie, and here he was playing this marine. It actually caused him a lot of discomfort. I don't think he enjoyed that, actually, getting into that psyche."<ref>{{cite news|url=https://www.avclub.com/lili-taylor-1798219253 |title=Lili Taylor |newspaper=The A.V. Club |date=March 10, 2010 |access-date=April 19, 2022 |first=Kyle| last=Ryan}}</ref>

Phoenix reunited with Keanu Reeves to co-star in [[Gus Van Sant]]'s 1991 avant-garde film ''[[My Own Private Idaho]]''. In his review for ''[[Newsweek]]'', David Ansen praised Phoenix's performance as gay hustler [[Mikey Waters|Michael Waters]]: "The campfire scene in which Mike awkwardly declares his unrequited love for Scott is a marvel of delicacy. In this, and every scene, Phoenix immerses himself so deeply inside his character you almost forget you've seen him before: it's a stunningly sensitive performance, poignant and comic at once". He won the [[Volpi Cup for Best Actor]] at the [[1991 Venice Film Festival]]. In addition, the 21-year-old Phoenix received [[Independent Spirit Award for Best Male Lead]] and [[National Society of Film Critics Award for Best Actor]], becoming the second-youngest winner of the former.<ref name="Sharf"/> His critically acclaimed performance helped bring [[queer cinema]] to a mainstream audience. The film and its success solidified his image as an actor with edgy, leading man potential. In that period, Phoenix was beginning to use [[marijuana]], [[cocaine]] and [[heroin]] with some friends.<ref name="people"/><ref name="High Life">{{cite journal |last1=Schindehette |first1=Susan |last2=Stambler |first2=Lyndon |last3=Dodd |first3=Johnny |last4=Benet |first4=Lorenzo |last5=Stone |first5=Joanna |name-list-style=and |date=January 17, 1994 |title=High Life |url=https://people.com/archive/cover-story-high-life-vol-41-no-2/ |journal=People |volume=41 |issue=2 |access-date=April 19, 2022}}</ref>

Around this time, Phoenix was approached by [[George Lucas]] to reprise his role of a younger Indiana Jones for ''[[The Young Indiana Jones Chronicles]]'', a spin-off television series produced by the [[American Broadcasting Company|ABC]] that served as a prequel to the ''Indiana Jones'' films. However, Phoenix declined to reprise the role due to having started his career in different sitcoms and struggled hard to get out from the television medium, not being willing to return to it. The role of a younger Indy was eventually filled by [[Corey Carrier]] and [[Sean Patrick Flannery]], respectively.<ref>{{cite web |url=http://www.theraider.net/films/young_indy/making_2_casting.php |title=The Making of ''The Young Indiana Jones Chronicles'' - Chapter 2: Casting |publisher=TheRaider.net |access-date=May 12, 2023 |archive-date=January 16, 2013 |archive-url=https://web.archive.org/web/20130116105011/http://www.theraider.net/films/young_indy/making_2_casting.php |url-status=live }}</ref>

He teamed up with [[Robert Redford]] and again with Sidney Poitier for the conspiracy/espionage thriller ''[[Sneakers (1992 film)|Sneakers]]'' (1992). A month later, he began production on [[Sam Shepard]]'s art-house ghost western ''[[Silent Tongue]]'' (which was released in 1994). He was beaten out for the role of Paul by [[Brad Pitt]] in ''[[A River Runs Through It (film)|A River Runs Through It]]''. Phoenix then starred in [[Peter Bogdanovich]]'s country music-themed film, ''[[The Thing Called Love]]'' (1993), the last completed picture before his death. He began a relationship with co-star [[Samantha Mathis]] on the set.