The Gregory Brothers

I love this group. They're extremely talented, happy and intelligent. They have a very comedic persona for most of their music; for instance, they've released a whole album about playing sad songs in happy styles, and vice versa... awesome. But I believe there's much more to the Gregory Brothers than their public, comedic personas (though by all means I love this aspect of their work and hope they continue to nurture it!!).
The group are very talented singers, songwriters and musicians. It's a pleasure listening to new takes on music. So... here's some good listening for you.

Song: Hello Again | Wrecking Ball - Country Version | DJ Play My Song | Good Morning Sarah | Always Summertime
Album: Hello Again - Single | Wrecking Ball - The Country Version | DJ PLay My Song (single) | The Lost Year | Always Summertime (single)
Artist: The Gregory Brothers

• Andrew Gregory
• Evan Gregory
• Sarah Gregory
• Michael Gregory

Genre: uncategorizable, but centered around: pop, country, blues
Youtubeable ?: Definitely! Perhaps the most Youtubable group so far reviewed.
Karaoke Difficulty: Extreme. While the songs aren't always difficult, nor the lyrics always complex in delivery, the quality of singing is always excellent. If you sing these songs well, at Karaoke, you'd win karaoke, but most people might not know the Gregory Brothers yet so while they would obviously sing your vocal praises they would wonder what you just sang.
Listenable ?: Highly Listenable.... The group is highly talented and the songs discussed are on my playlist of "Best Music Ever."
Popularity: Hmm... depends on which aspect of the Gregory Brothers you are referring to:

• Autotune the News: some popularity
• Singles of iTunes (like Double Rainbow song, Bed Intruder Song): Very popular
• More serious recordings (The Lost Year, Meet the Gregory Brothers, etc): less popular.

Notable Song(s) by Artist:

• Autotune the News
• Double Rainbow Song
• Bed Intruder Song

How I First Learned About the Gregory Brothers (and Sister Brother): 
Autotune the News is one of the greatest things on the internet and I wish more were done. They are catchy and smart and hilarious and great to listen to on repeat (many days of work have passed listening to the Autotune the News tracks).
Other Tracks to Listen to:

• West Coast Time
• A Wonder
• Do You Think

The Songs

You can find all of these songs on Spotify.

Hello Again:

The singer (Michael Gregory) has a great voice, able to get a clear sharpness from single notes that can cut through and get right to your inner listening. Also really appreciate the arrangement, from the strong bass line that plays a focal point in the song (and not just a subconscious supporting role). Lyrically, this song really hits home for me. The number of times I've felt this way kinda wrecks me sometimes, and in that, this song is able to produce a feeling in the still deep quiet of my emotions. We are all suckers for feeling something true or present in ourselves. The supporting voices are also well done. All in all... love this song, from start to finish.

Wrecking Ball - The Country Version

I'd classify this as a bluegrass version of "Wrecking Ball." The best part of this song are the layered vocals during the refrain.I'm always partial to bluegrass and so hearing this pop song turned bluegrass was a treat. In addition though, the Gregory Brothers really understood the genre and recreated the song faithfully inside a different genre. The instrumentation is a single snare, a bango and a guitar. This song is worth listening to, multiple times.

DJ Play My Song

Are you tired of mindless pop music? Do you wish someone would spoof by masterfully creating an earworm of a pop song, and then mocking it? Best part of this song is the conversational back and forth between the lead female (Sarah Gregory) and the DJ (Evan Gregory). Listen to the lyrics. They are hilarious. On top of the cerebral hilarity, the song is well crafted and sung. Kudos Gregory Brothers for your ability to diversify and still succeed.

Good Morning Sarah

I listen to this song non-stop, on repeat, for hours. This song speaks to ancient parts of me in ways that I can't explain, like the music that calms the lion, this song brings a wave of peace immediately and it delivers that peace the whole way through. The layered guitars and brush snare really define the whole song, and the vocals of Andrew Gregory take the song beyond. I cannot state how much I love listening to this song.

Always Summertime

This really shows off the strong vocals of Sarah Gregory (who's technically more of a sister brother, than a brother brother, because girl. Also, this is the Gregory Brother's own classification of Sarah Gregory... so I cannot claim that spot of comedy gold, though were I buoyed by scruples of a lesser quality then I'd totally steal that joke and ride that fame all the way to the Daily Show. le sigh).

The song is an amazing paradox in that it is very peppy and sunny but the lyrics are so opposite. I chalk this up to the playful and intellectual experimentation of the Gregory Brothers. And again... amazing talent.