"Yale, you've made me white and blue for you," Milestone sings while playing guitar. "Yale, if you let me in, I'll show you just what I can do for you."
As of Friday, the video had received nearly 21,000 views and the attention of at least students at the college in New Haven, Conn.
"She is competitive," wrote one who saw the video via a link on the website of the Yale Daily News.
"This video is clever and a sign of high motivation - and a pledge to demonstrate to Yale that a decision to admit her will prove wise."
Thomas Conroy, a spokesman from Yale, declined to say whether the admissions office saw Milestone's almost four-minute music video. Conroy said the college does not discuss individual applicants' status.
For undergraduate admissions, Yale received 4,304 early-action applications for the Class of 2016 and issued 675 admissions offers.
Yale expects to make an additional 1,300 to 1,500 offers, and the video, shot in the senior's hometown of Narberth, shows Milestone is determined to be one of them.
It is a result of several weeks' worth of Milestone's songwriting, sound editing by Lower Merion High School students, and film work by her 21-year-old sister, Jessie.
Stefan Richter and Jake Goodman, both seniors at Lower Merion High School, used the recording studio they started, BamBam Studios, to help their Harriton peer edit her sound and add other guitar sounds, bass, and percussion.
"My sister certainly spent a lot of time putting it together," Milestone said. "Stefan and Jake are good friends. . . . it's the first time I've made my music public, really, and I'm pretty excited about it."
If Milestone's video performance seems polished, it is in part because she performs at open-mic nights at venues like Ardmore's MilkBoy.
Milestone is an editor at the Harriton Banner, the school newspaper, and the Corinthian, the creative writing magazine. She loves reading and studying literature, but she loves singing and songwriting just as much, if not more. It's something she said she would include in her life, incorporating it as career or a lifelong hobby.
For the moment, however, it has been harnessed in service to her collegiate dream.
"If things don't work out, I'll find another school where I can be happy," Milestone said. "I just have a lot of goals and ambitions, and I really want Yale to be the place I thank when I accomplish them."
Watch Jackie Milestone's video at
Contact Josh Fernandez at firstname.lastname@example.org.