A former White House aide to President Bill Clinton, Boykin was raised in St. Louis, Missouri, and attended Countryside High School in Clearwater, Florida, before graduating from Dartmouth College.

After leaving Dartmouth in 1987, Boykin spent a year and a half working for Michael Dukakis' presidential campaign and then entered Harvard Law School, where he was a leader in the campus diversity movement and general editor of the Harvard Civil Rights-Civil Liberties Law Review. He received his J.D. from Harvard in 1992 and then joined the Clinton/Gore Campaign in Little Rock, Arkansas. After Clinton's election, Boykin became a Special Assistant to the President and Director of Specialty Media. Once the highest-ranking openly gay person in the Clinton White House, Boykin helped organize and participated in the nation's first meeting between gay and lesbian leaders and a U.S. President.

Boykin left the White House to write his first book, Black and Gay in America, published in 1996. He released his second book, Respecting the Soul, in 1999.

In 1997, Clinton appointed Boykin to the U.S. presidential trade delegation to Zimbabwe, along with Rev. Jesse Jackson, Coretta Scott King and Transportation Secretary Rodney E. Slater. From 1999 to 2001, Boykin taught political science at American University in Washington, D.C.

Boykin appeared on the Showtime television series American Candidate and has appeared on VH1, BET, CNN, Fox News, NPR, and numerous other television and radio programs, including The Montel Williams Show, The Dennis Miller Show, The Tom Joyner Morning Show, Tony Brown's Journal and Anderson Cooper 360°. He has been featured on the cover of several publications including A&U, Out and The Advocate, and he was selected as one of Out magazine's 100 Most Intriguing People of 2004. He has also been featured or quoted in articles in the New York Times, The Washington Post, USA Today, Vibe and Jet.

He has written for the Village Voice, the San Francisco Chronicle, the St. Petersburg Times, The Advocate, Black Issues Book Review, and The Crisis. His syndicated column appears in several newspapers across the country, including the New York Blade, the Washington Blade, Southern Voice and Houston Voice.

As of October 2008, Boykin was making regular appearances on CNN, MSNBC, CNBC, BET and BET J. He appeared on CNBC for coverage and analysis of the three presidential debates and one vice presidential debate. He also covered the Democratic Convention for BET from the floor of the Pepsi Center and Invesco Field in Denver, Colorado.

In February 2006, Boykin became a co-host of the TV series My Two Cents on the BET J channel, a part of BET Networks. In January 2007, he began making regular appearances as a commentator on CNN and he also appeared on Judge Hatchett.

Boykin's most recent book, Sex, Lies and Denial in Black America focusing on the down-low phenomenon, was published in February 2005 and released in paperback in February 2006. From December 2003 until April 2006, Boykin served as president of the board of the National Black Justice Coalition, a Washington-based civil rights organization dedicated to fighting racism and homophobia. He lives in New York City.