Garcia attended Lower Merion High School and Wesleyan University (class of 1988).
Bobbito initially started as an intern at Def Jam Records.
From 1990-98, Garcia co-hosted The Stretch Armstrong and Bobbito Show on WKCR. It featured exclusive demo tapes and in-studio freestyles from many then-unsigned hip hop artists such as Nas, Big Pun, Jay-Z, Busta Rhymes, Fat Joe, Cam'ron, DMX, Wu-Tang Clan, Fugees, Talib Kweli, Big L and The Notorious B.I.G. who later found great success on major record labels.
He set up the vinyl-only label Fondle 'Em Records in 1995 as an outlet for other guests such as MF DOOM, MF Grimm, Kool Keith and Cage. In 1998, The Source named The Stretch Armstrong and Bobbito Show as the "Best Hip Hop Radio Show of All Time".
In 2000, hip hop artist Necro included a Live freestyle from a Bobbito WKCR show recorded on 4/20/2000 on his debut album "I need Drugs". The two have collaborated as early as 1994. In 2003, García created Bounce: From the Playground, a quarterly magazine devoted to streetball, especially the playground scene in New York City. He has been an editor, writer, and photographer for the magazine, and has also done work for and been featured in magazines including Vibe and The Source.
He was featured in a 2002 article in Vibe Magazine.
Bobbito Garcia hosted the ESPN Films It's the Shoes, interviewing celebrities about their sneaker collection. He was featured in the sneaker documentary Just for Kicks and performed the announcer's voice in NBA Street Vol. 2, NBA Street V3 and NBA Street Showdown. He is emcee of the Sprite Slam Dunk Contest in the video game NBA 2K8, 2K9 and 2K10. He wrote Where'd You Get Those?: New York City's Sneaker Culture 1960-1987 as well as Out of the Box, about limited edition sneakers.
In 2007, he worked with Nike on limited edition Nike Air Force 1 and Air Force 25 models, selecting the colors, fabrics and logo used, and designed the "Project Playground" limited edition of the Adidas Superstar. In 2016, he collaborated with Puma for a brand of sneakers.
In 2006, Madison Square Garden Network hired García to do the "Hot Minute at the Half" reports with celebrities in the crowd during Knicks home games. He became the first Latino broadcast member in the 60-year history of the franchise.
In 2009, he worked on Blokhedz animated web series on Missiong.com. Garcia is the annual Boost Mobile Elite 24 HS All-American Game play-by-play announcer for ESPNU, owner of the vinyl-only label/imprint Álala Records, and co-directing a documentary, Doin' It In The Park: Pick-up Basketball, New York City, produced by 360 Creative Films, which premiered in New York theaters in June 2013. Bobbito has his own basketball tournament called Bob’s Full Court 21, which he holds around the nation.
Another testament to his influence in basketball culture is his character as an announcer in the popular 2003 video game by Electronic Arts, NBA Street: Vol. 2. He also served as a consultant for EA, contributing his knowledge of the street basketball and New York cultures.