Question: Which Broadway play did Anthony Rapp begin his singing and songwriting career with?

Context paragraphs:
Adventures in Babysitting: Adventures in Babysitting (also known as A Night on the Town in certain countries) is a 1987 American comedy film written by David Simkins, directed by Chris Columbus (in his directorial debut), and starring Elisabeth Shue, Maia Brewton, Keith Coogan, Anthony Rapp, Penelope Ann Miller, Bradley Whitford, and brief cameos by blues singer/guitarist Albert Collins and singer-songwriter Southside Johnny Lyon.

Look Around (Anthony Rapp album): Look Around is the first full-length album by American actor/singer Anthony Rapp, known as a singer for his performance as Mark Cohen in the musical Rent and the film adaptation of the musical.  It was released on October 1, 2000.

Eric Schwartz (songwriter): Eric Schwartz (Eric "Red" Schwartz) is an American folk singer/songwriter and musical satirist known for his often humorous, sexually explicit lyrics, as in the songs "Clinton Got A Blowjob" and "Who Da Bitch Now".  His video, "Keep Your Jesus Off My Penis" has been downloaded over a million times.  He cites Dr. Demento as an inspiration.  He graduated from Tufts University with a degree in biology and worked as an actor and guitarist, before moving to Greenwich Village to begin his songwriting career.  He has played several times at the Kerrville Folk Festival and was a finalist in the songwriting contest in 2001.  He was a winner of the Falcon Ridge Folk Festival Emerging Artist Showcase.

Risley Residential College: Prudence Risley Residential College for the Creative and Performing Arts, commonly known as Risley Residential College, Risley Hall, or just Risley, is a program house (themed residence hall) at Cornell University.  Unlike most other dormitories on campus, Risley is a residential college; house members, or "Risleyites," have some say in the administration of the residence hall, can continue to reside there as long as they are enrolled at Cornell, are encouraged to eat together at the in-house dining hall, and participate in educational activities such as guest lectures within the dormitory.  The building houses 192 students, chosen by Risleyites from a number of applications, as well as one or two Artists-In-Residence ("AIRs"), who live in the building and organize regular programs in which the house members participate.  Currently, Risley's Artist-In-Residence is Adam J. Boggs.  Previous AIRs include Patrick Gray, Carolina Osorio-Gill, Natalie Tyler, Abraham Burickson, Gregory Halpern, and Brandon Bird.  Many famous people have visited the house for intimate discussions with the Risleyites, such as Anthony Rapp, John Cleese, who hosted a question and answer session after the showing of his film "A Fish Called Wanda", and Samuel R. Delany who continues to collaborate with Risley alumnus Kenneth James.  .

Man of the Century: Man of the Century is a 1999 comedy film directed by Adam Abraham and written by Abraham and Gibson Frazier.  The film stars Frazier, Cara Buono, Susan Egan, Dwight Ewell and Anthony Rapp.  It is a farce about the attitudes, values, and slang displayed in the popular culture of the 1920s (and, to some extent, the early 1930s).  "Man of the Century" was filmed in black and white.  Its working title was "Johnny Twennies".

Without You (book): Without You: A Memoir of Love, Loss, and the Musical Rent is a 2006 memoir by a musical theater actor, Anthony Rapp.  Later it was turned into a staged musical adaptation by the same name.

Selda and Derek: Selda and Derek are an American songwriting duo, consisting of Selda Sahin (lyrics) and Derek Gregor (music), best known as the songwriters of the musical film Grind, starring Anthony Rapp, Claire Coffee and Pasha Pellosie.  They are co-writing Eric Michael Krop's pop album "Greater Things", to be released in 2016.

School Ties: School Ties is a 1992 American sports-drama film directed by Robert Mandel and starring Brendan Fraser, Matt Damon, Ben Affleck, Chris O'Donnell, Cole Hauser, Randall Batinkoff, Andrew Lowery and Anthony Rapp.  Fraser plays the lead role as David Greene, a Jewish high school student who is awarded an athletic scholarship to an elite preparatory school in his senior year.

Open House (2004 film): Open House is a 2004 real estate musical film starring Hedy Burress, Ann Magnuson, Anthony Rapp, Sally Kellerman, Jenna Leigh Green and Kellie Martin, and directed by Dan Mirvish, a co-founder of the Slamdance Film Festival.  It played on the film festival circuit in 2004–05 and was released on DVD through Wellspring Media.  All the actors sang live on set, rather than lip synching.

Anthony Rapp: Anthony Deane Rapp (born October 26, 1971) is an American stage and film actor and singer best known for originating the role of Mark Cohen in the Broadway production of "Rent" in 1996 and later for reprising the role in the film version and the Broadway Tour of "Rent" in 2009.  He also performed the role of Charlie Brown in the 1999 Broadway revival of "You're a Good Man, Charlie Brown" and originated the role of Lucas in the musical "If/Then" in 2014.

Supporting paragraphs: Selda and Derek Anthony Rapp
Answer: "Rent"