Lisa Loeb "Stay"

If you were a teenage boy in the 1990s, chances are you had a crush on Lisa Loeb.  With her girl-next-door looks and patented throwback glasses, Loeb adorned the hearts of many hormonal teens in 1994.  Present company included.  Loeb burst onto the scene when her folksy tune "Stay (I Missed You)" appeared on the Reality Bites Soundtrack.  The song quickly shot up the music charts and landed on the #1 spot in 1994 despite Loeb not having a record contract.  It was a feat not accomplished again until a recording contract-less Macklemore (featuring Ryan Lewis) did it in 2013 with "Thrift Shop".

Lisa Loeb - "I Do"

Does any one else ever wonder if Lisa Loeb was paid by the Optometry Association of America for wearing those throwback glasses simply so that girls would run out and buy eyeglasses?  No?  Okay, never mind...

Lisa Loeb - "Do You Sleep?"

There was a long stretch of my life where I was absolutely smitten with Lisa Loeb.  She was the (then) modern-day Winnie Cooper: the cute, petite, girl-next-door with those hot throwback glasses (Winnie also wore glasses in early episodes of The Wonder Years).  Years ago, I had the pleasure of meeting her and my colleague immediately told her that I had had a giant crush on her since high school.  As the awkwardness permeated the room, I stood there dumbfounded with this black and white head shot of her that I was hoping to have her sign.  I awkwardly mumbled, "Um, could I get you to autograph this picture?"  She smiled politely and wrote: "Thanks for listening" on the photo.  It was a very politest brush-off that reminded me of all the times I failed at asking girls out in high school.