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What's Up Magazine

The Best Of Best Of

Jun 07, 2018 04:00PM ● Published by Brian Saucedo

By Cate Reynolds and Caley Breese

Thursday, June 14th marks the 15th annual What’s Up? Media Best Of Party. This yearly event celebrates our Best Of winners and our amazing readers. In honor of this exciting milestone, let’s take a trip back to yesteryear and reflect on the best of Best Of. 


2004 was the year Facebook launched, but more importantly, it was the year of the very first Best Of Party. 

Party theme: Best Bash Inaugural Party

#1 Song That Year: Yeah! - Usher feat. Lil Jon and Ludacris

Biggest Fashion Trend That Year: Hoop Earrings, Halter Necks, Suede Boots

Auction benefit: Maryland Hall for the Creative Arts


In 2005, we were graced with NBC’s “The Office,” as well as the second annual Best Of Party. 

Party theme: Le Cirque Magnifique

Auction benefit: Maryland Hall for the Creative Arts; Ballet Theater of Maryland; The Annapolis Chorale; Annapolis Symphony Orchestra; Annapolis Opera

#1 Song That Year: Gold Digger - Kanye West feat. Jamie Foxx

Biggest Fashion Trend That Year: Cargo Pants and Juicy Tracksuits


In true Oscar style, the 2006 Best Of Party featured commentary by Joan Rivers and a special appearance by Marilyn Monroe!

Party theme: A Night at the Oscars

Auction benefit: Maryland Hall for the Creative Arts; Ballet Theatre of Annapolis; Annapolis Opera; Annapolis Chorale

#1 Song That Year: Bad Day - Daniel Powter

Biggest Fashion Trend That Year: Babydoll and slip dresses


In 2007, Apple took a step into the future of technology by releasing the very first iPhone. Meanwhile, the Best Of Party traveled back in time to the roaring '20s.

Party theme: Jazz Age (‘20s)

Auction benefit: Maryland Hall for the Performing Arts

#1 Song That Year: Irreplaceable - Beyoncé

Biggest Fashion Trend That Year: Denim mini-skirts with cropped leggings 

Staff memory: “We had gangsters and mobsters manning the entrance to the hotel, flapper dancers in the lobby, and all manner of thematic decor inside. It truly felt like the most elaborate and cohesively themed party. It was a blast!”-  James Houck, Editorial Director


At the 2008 Best Of Party *NSYNC member Chris Kirkpatrick made an appearance, officially winning Best Of *NSYNC. 

Party theme: Masquerade

Auction benefit: Maryland Hall for the Creative Arts; Modest Needs; Chesapeake Bay Environmental Center

#1 Song That Year: Low - Flo Rida feat. T-Pain

Biggest Fashion Trend That Year: Leggings for pants - tight and/or bright


Chris Kirkpatrick couldn’t say “Bye Bye Bye” to the Best Of Party and returned to the 2009 party for a second year of fun!

Party theme: Tip Your Hat to the Best (Outrageous Hat Contest)

Auction benefit: Historic Annapolis Foundation and Chesapeake Bay Environmental Center

#1 Song That Year: Boom Boom Pow - Black Eyed Peas

Biggest Fashion Trend That Year: One Shoulder Dresses


In 2010 we showed off our Maryland and Annapolitan pride by hosting the very first nautical themed Best Of Party. It proved to be a crowd favorite, and has been a recurring theme in recent years.

Party theme: Nautical 

Auction benefit: Environmental Concerns and five Annapolis nonprofits

#1 Song That Year: Tik Tok - Ke$ha

Biggest Fashion Trend That Year: Sequin Shorts


Qui qui! In 2011, we celebrated the Crème de la Crème at our très magnifique Best Of Party.

Party Theme: Crème de la Crème 

Auction benefit: Wellness House of Annapolis

#1 Song That Year: Rolling in the Deep - Adele

Biggest Fashion Trend That Year: Hair feathers and colored denim


In 2012 we saw the rise of Instagram, just in time for red carpet photo ops at our Party with the Stars Best Of Party. 

Party Theme: Party with the Stars

Auction benefit: Hospice of the Chesapeake and Chesapeake Bay Maritime Museum 

#1 Song That Year: Somebody That I Used To Know - Gotye feat. Kimbra

Biggest Fashion Trend That Year: Peplum shirts and dresses


2013 brought Maryland a Superbowl championship (Go Ravens!). Best of attendees may have been wearing masks, but no one was masking their excitement. 

Party Theme: Venetian-style Masquerade 

Auction benefit: Anne Arundel County Library Foundation and Hospice of Queen Anne’s County

#1 Song That Year: Thrift Shop - Macklemore and Ryan Lewis feat. Wanz

Biggest Fashion Trend That Year: High waisted shorts, plaid prints, skater dresses


In 2014, just like the rise of Instagram, we also saw Snapchat become more popular—perfect timing for party-goers to show off their classic white attire.

Party Theme: White Hot Night

Auction Benefit: Community Foundation of AAC and Phillips Wharf Environmental Center

#1 Song That Year: Happy-Pharrell Williams

Biggest Fashion Trend That Year: Pleated skirts and bucket bags

Staff memory: “This was my favorite Best Of Party. The thrill was to see what everyone decided to wear and to hear from our readers ‘there isn’t anything left on the racks at local boutiques that is white!’” - Ashley Raymond, Chief Operating Officer


2015 saw one of Maryland’s rainiest Junes on record, but it was nothing but clear skies and smooth sailing at our 2015 party.

Party theme: “Winner’s Tonight, Sailor’s Delight” Sailing Whites

Auction benefit: Anne Arundel Medical Center; Friends of Anne Arundel County Animal Control; Maryland Theatre for the Performing Arts; Chesapeake Bay Maritime Museum; YWCA; and South River Federation

#1 Song That Year: Uptown Funk! - Mark Ronson feat. Bruno Mars

Biggest Fashion Trend That Year: White Sneakers and button-down skirts


In 2016, Leonardo DiCaprio won his first Oscar and our ever-popular nautical theme made a reappearance. Two equally exciting events! 

Party theme: Nautical

Auction benefit: SPCA of Anne Arundel County; Talbot Humane Society; and other local charities

#1 Song That Year: Love Yourself - Justin Bieber

Biggest Fashion Trend That Year: Chokers, ripped denim, velvet


In 2017, Taylor Swift made a comeback and so did our nautical theme. Again, two spectacular events.

Party theme: Nautical

Auction benefit: South River Federation; Chesapeake Bay Maritime Museum; and other local charities

#1 Song That Year: Shape of You - Ed Sheeran

Biggest Fashion Trend That Year: Puffer jackets, extended sleeves


The 2018 Best Of Party is one week away, and it’s not too late to join the fun! Tickets are still available at Throw on your best nautical attire and get ready for a night filled with award-winning food, live entertainment, and a whole lot of fun. This year’s silent auction will benefit the YWCA of Maryland and Haven Ministries.

Silent auction items include a Disney World family adventure, a four-night stay at the Fairmont Southampton in Bermuda (including airfare for two!), a spa package by Sandel Duggal, an Island Tackle Outfitters Yeti Roadie Cooler, and much more. 

Don’t forget your dancing shoes! We’ll have a DJ playing some great tunes so you can boogie down on the dance floor. Be sure to capture the night by striking a pose at our photo booth, or getting your caricature drawn. Did we mention all the delicious food provided by our Best Of winners? Indulge in mouth-watering dishes including a charred black pepper tuna appetizer from Mother’s, Southern pickled shrimp crostini with avocado mash and micro greens from Miss Shirley’s, carved tenderloin and mashed potatoes from Ruth’s Chris Steakhouse, and a macaroni and cheese bar from Main & Market.

It’s going to be the party of the year, and you don’t want to miss it!

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